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Holiday Vacation Rentals for Families and Groups

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Modern Resort-Living Compound
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(Someone Else's) Home for the Holidays

Thinking of getting away with family and/or friends for the holidays? Now is the time to book — we're seeing vacation rental properties get snatched up quickly already. If you're already looking to late 2021 and beyond to plan a reunion or extra time with loved ones — whether they be family by blood or choice — here are some multi-home properties, mansions, and other large-group-worthy rentals across the U.S. that offer everybody some space of their own. After all, just because it will eventually be safe to hug and laugh and cry together in person again doesn't mean everybody wants to be on top of one another, right?


Prices and availability are subject to change.


Related: 30 Mansions You Can Actually Afford to Rent

Hill Country Compound
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Hill Country Compound
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Hill Country Compound: More

Each rental unit has a porch, and the "barn" has both front and back porches, each with a table for outside dining, seating up to 22. The waterfront is a quick 30-second walk away.

Decadent Five-House Compound
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Decadent Five-House Compound

Hollywood, Florida | Sleeps 20
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Billing itself as "one of the single largest, most unique rentals in South Florida," this property includes five private homes featuring recent upgrades that share a large yard.


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Decadent Five-House Compound
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Decadent Five-House Compound: More

The homes are all situated around a fenced-in pool with an integrated 10-person hot tub. It's unlikely anyone will get bored here — other amenities include a pool table, volleyball, tetherball, a barbecue grill, and much more.

Indie Style
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Indie Style

Chicago | Sleeps 16

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Logan Square has been one of Chicago’s destinations for music and art since the 1990s, and this home provides access to it all, with both privacy and peace in the main house, guest house, and in the backyard that joins them. As you stroll N. Milwaukee Blvd., you’ll find both upscale dining and the area’s longtime Latino establishments. 

Indie Style: More
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Indie Style: More

Fourteen-foot windows on the first floor fill the space with light. The open plan features a solid-wood dining table, a stylish contemporary living room, and a modern kitchen with an island for extra seating. 

Lions Gate Estate
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Lions Gate Estate

Atlanta Area | Sleeps 20
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An estate with gravitas, Lions Gate is a whopping 18,000 square feet — more than enough room for most to spread out and claim their own space. Marietta is only 15 miles from Atlanta, but explore the area to experience the town's main attraction: The Big Chicken.

Lions Gate Estate: The Pool
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Lions Gate Estate: More

The pool and hot tub are nestled in a stone-covered wonderland, which gives the outside area the feeling of a spa. Make plans to live outside during your stay, as the separate pool house has a grill and an outdoor kitchen. Or take advantage of other amenities like the property's theater, Irish pub, billiards room, and more. 


Newhouse Manor
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Newhouse Manor

Dallas | Sleeps 18
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Reunions, fancy fishing trips, quality time with one’s horses — this sprawling estate pleases vacationing humans and equines alike, featuring a separate fenced-in yard and an open barn for stalling.


Newhouse Manor
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Newhouse Manor: More

Guests who can bear to part with the prepossessing property and its toys (trampolines, a pool, hot tub, a half basketball court) will find Cedar Hill State Park, with its rugged limestone hills and hiking trails, and Joe Pool Lake, less than five miles away, not to mention Texas’ largest zoological experience, the Dallas Zoo, within 10 minutes.


Related: The Best Lakefront Vacation Rentals Across America for a Peaceful Getaway

Lakefront Family Compound and Lodge
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Lakefront Family Compound and Lodge

Northeast Somerset, Maine | Sleeps 10-11
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Featuring four early 20th-century cabins situated near the banks of Moosehead Lake, this waterfront rental property offers stunning sunsets and plenty of space to explore.

Lakefront Family Compound and Lodge
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Lakefront Family Compound and Lodge: More

With five bedrooms, this property sleeps 10 and is off-grid — so you can truly escape daily life for some time with family or friends. 

Nanaquaket Cove Family Compound
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Nanaquaket Cove Family Compound

Tiverton, Rhode Island | Sleeps 14
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With this rental, you'll get a main house and guest house on 3 acres with 250 feet of shoreline along Nanaquaket Cove. The house comes with games and a large kitchen perfect for preparing large holiday meals. 

Nanaquaket Cove Family Compound
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Nanaquaket Cove Family Compound: More

The guest house has lower and upper decks that look out onto the water. There is also an outside patio with a seating area for meals al fresco.

Key West Compound
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Key West Compound

Key West, Florida | Sleeps 22
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This property consists of five separate rentals that all share a pool, a large outdoor area, sundeck, and bar. It's also located on Duval Street, known for its restaurants, nightlife, and regular community events.

Key West Compound
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Key West Compound: More

The light, bright homes are tastefully decorated with tropical-themed decor and cheerful colors. Each rental comes with Wi-Fi and cable TV, too.

Eight-Acre Private Resort
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Eight-Acre Private Resort

Cashiers, North Carolina | Sleeps 18
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Gather the loved ones for a vacation in western North Carolina — near both the South Carolina and Georgia border. This unique property includes three rental homes with seven porches and decks between them that offer great views of the surrounding vistas and plenty of places to hang out with a cup of coffee or a cocktail.

Eight-Acre Private Resort: More
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Eight-Acre Private Resort: More

An open-concept living space offers plenty of room to spread out and enjoy family time. 

San Cristobal Cabins
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San Cristobal Cabins

San Cristobal, New Mexico | Sleeps 40
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With a lodge that sleeps 26, and nine cabins that collectively sleep up to 14, this property — located about half an hour north of Taos — can accommodate a crowd. 

San Cristobal Cabins
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San Cristobal Cabins: More

The rental is a great option for people who don't mind roughing it a bit and enjoy nature. There are rescue animals on the site as well as chickens, fresh vegetables and eggs are available seasonally, and the land is filled with creeks, ponds, trees, gardens, and more to explore.

Modern Resort-Living Compound 2
Expedia
Modern Resort-Living Compound 2
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Modern Resort-Living Compound: More

Other amenities include multiple fire pits, fountains, a grilling area, and a large pool and spa.

Dimora Di Lusso
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Dimora Di Lusso

Atlanta | Sleeps 25
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The Dimora Di Lusso brings Tuscany to the South by way of Georgia. Floor-to-ceiling windows and a terrace created for lounging give the villa an upscale-yet-cozy flair. Sandy Springs is just a half-hour outside Atlanta, and a hop, skip, and a jump away from Buford Highway, a destination spot for international cuisine.

Dimora Di Lusso: The Pool
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Dimora Di Lusso: More

The pool and surrounding decor at the Dimora Di Lusso are straight out of a five-star resort. Luxuriate under the individual waterfalls in the pool. Inside, the high, vaulted ceilings in the main bedrooms will make your jaw drop. 

Lavish Celina Ranch
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Lavish Celina Ranch

Dallas | Sleeps 16 

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Without leaving the site, this property perchance meets the R&R-related desires of every weary traveler in the gang. From the ping pong-, foosball-, air hockey-, and double poker table-equipped game room to a fully appointed kitchen and outdoor dining area plus firepit, each lavishly rustic room of the 5,100-square-foot estate tempts one to stay and savor the amenities.

Lavish Celina Ranch
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Lavish Celina Ranch: More

Nevertheless, charming Downtown Celina, Texas, with its precious boutiques and bistros, located just outside the three-acre ranch, beckons. And downtown Dallas is but a half-hour jaunt.

Bella Vista Estate in Steamboat Springs, Colorado
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Bella Vista Estate

Steamboat Springs, Colorado | Sleeps 28
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You might call this Rocky Mountain high living. Just minutes from downtown Steamboat, Bella Vista Estate is a 7-acre rental with panoramic mountainside vistas. The luxury estate includes three different homes with a total of 12 bedrooms, 10 bathrooms, and two half baths. 

Bella Vista Estate: More
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Bella Vista Estate: More

There are four fireplaces, a great room, a heated swimming pool, a tennis court, game room, and pool table. And chauffeur service is available for trips into downtown Steamboat.

Captain Morse House in Edgartown, Massachusetts
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Captain Morse House

Edgartown, Massachusetts | Sleeps 26
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Who wouldn’t want to rent a mansion for vacations on the East Coast's famed Martha’s Vineyard? The stately Captain Morse House was built in 1840 by the whaling captain in the Greek Revival style and is conveniently located near shopping areas and four beaches. 


Captain Morse House | More
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Captain Morse House | More

The historic 8,000 square-foot house offers 12 bedrooms, seven baths, and two full kitchens along with a roomy backyard and a patio. 

The Wolcott
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The Wolcott

ChicagoSleeps 16

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This home in lively Wicker Park makes a striking presence on its corner lot with a three-story brick and glass facade. The back courtyard mixes grass with slate tiles and is marked by the painted mural on the brick building next door. Rooftop decks include a basketball hoop and a hot tub for a truly luxurious stay. While in the neighborhood, you can visit Wicker Park’s clubs, bars, and funky boutiques.

The Wolcott: More
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The Wolcott: More

The home includes six bedrooms and six bathrooms, a workout room, wine cellar, game room, and pool table. Furnishings are modern yet comfortable. Don’t miss the skyline view from that rooftop lounge. There are multiple living rooms with TVs, as well as a private parking garage. 

Tir Na Nog in Lake Villa, Illinois
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Tir Na Nog

Lake Villa, Illinois | Sleeps 24
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The perfect place to book for golf fanatics, Tir Na Nog is a private country estate with its own 9-hole course. For non-golfers, there’s still plenty to enjoy, such as fishing on Deep Lake, basketball, tennis, and lawn bowling. 

Tir Na Nog | More
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Tir Na Nog | More

Located just an hour's trip from Chicago’s O’Hare International Airport, the estate sits on 80 acres and has 10 bedrooms and nine bathrooms, two kitchens, and a gym.

The Sophisticate
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The Sophisticate

Atlanta | Sleeps 10
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Straight out of an old-school Hollywood movie, this 1920s charmer boasts luxe furnishings and designer touches. The hosts provide guests with super cozy pillow-top mattresses and cloudlike sheets.

The Sophisticate: The Pool
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The Sophisticate: More

After a dip in the pool, grab your racquet and play on the estate's private tennis court. Tennis not your style? No problem, shoot a few hoops on your own basketball court. There's also a theater room, pool table, and lushly landscaped courtyard on the property. 

Hudson River House in Catskill, New York
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Hudson River House | More
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Hudson River House | More

Other amenities include a game room, dining and sitting rooms, a music room, and a tennis court. The 10,000 square-foot rental has 11 bedrooms, seven baths, and one half bath.

Kill Devils Hill in Outer Banks, North Carolina
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Outer Banks Oceanfront Estate

Outer Banks, North Carolina | Sleeps 32
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Guests will have plenty of room to stretch out in this 8,200 square-foot home on the beach in Kill Devil Hills, North Carolina. The house has 12 bedrooms, 12 baths, and 3 half baths, along with its own pool billiard room, and a home theater with seating for 14. 


Related: 34 Amazing East Coast Beach Houses to Rent

Outer Banks Oceanfront Estate | More
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Outer Banks Oceanfront Estate | More

With nearby access to the Wright Brothers Memorial and many other attractions, it offers plenty of seaside fun and has a cabana with a full bath.

Middle River Castle in Fort Lauderdale, Florida
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Castle on the Middle River | More
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Castle on the Middle River | More

Inside are regal amenities like a 40-foot bar and breathtaking 35-foot ceilings. Amateur chefs will enjoy the house’s gourmet kitchen, which has multiple stoves, perfect for cooking up the day’s catch. There's also no shortage of nearby restaurants. 

Reading Farms Estate in Reading, Vermont
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Reading Farms Estate

Reading, Vermont | Sleeps 46
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Located in central Vermont, Reading Farms Estate sits on 400 gorgeous acres and is just minutes away from the Killington and Okemo ski areas. The 25,000 square-foot central property is the very image of New England charm and has been featured in Architectural Digest and House Beautiful. 


Reading Farms Estate | More
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Reading Farms Estate | More

At the heart of the estate is an 18th-century brick farmhouse. There are formal gardens and even access to a helipad. Other amenities include a library, gym, pool, and arcade game room. 

Mansion Belle Oasis in Las Vegas, Nevada
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Mansion Belle Oasis

Las Vegas, Nevada | Sleeps 30
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Looking to take a big group on a Las Vegas vacation while avoiding expensive hotel costs? The Mansion Belle Oasis is less than 10 minutes from McCarran Airport, so the vacation can start almost as soon as the plane lands. The luxurious contemporary mansion's ample backyard is a great spot to congregate, with a swimming pool, hot tub, and gazebo. 


Mansion Belle Oasis | More
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Mansion Belle Oasis | More

The professionally equipped kitchen will thrill cooks in the group, and the game room that houses a pool table, poker tables, and gaming consoles will please just about anyone. 

Whispering Pines in Eagle River, Wisconsin
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Whispering Pines Lodge

Eagle River, Wisconsin | Sleeps 40
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For a memorable North Woods trip, Whispering Pines Lodge will not leave anyone disappointed. A massive lakeside rental with huge windows to enjoy the sunset over Voyageur Lake, the lodge has an open, rustic decor with 30-foot ceilings, a majestic fireplace, and a lakeside hot tub. It is also located in an angler’s paradise on a huge chain of lakes near the Chequamegon-Nicolet National Forest. 



Whispering Pines Lodge | More
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Whispering Pines Lodge | More

There are 11 bedrooms and seven bathrooms, along with an easy-access carport and family-friendly amenities like a playground and a sandy beach for the kids.

Lake Burton House in Clarkesville, Georgia
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Lake Burton Home

Clarkesville, Georgia | Sleeps 20
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Located on Lake Burton in the Nantahala National Forest near the North Carolina border, guests who book a trip to this retreat will enjoy this home’s rustic oak and pine decor and exquisite lake views. 

Lake Burton Home | More
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Lake Burton Home | More

There are eight bedrooms, nine baths, two half baths, a stone fireplace, a three-story room with a vaulted ceiling. There’s also access to a two-story boathouse and a protected swimming area.

Red Feather Lodge
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Red Feather Lodge

Big Sky, Montana | Sleeps 28 
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This custom, 7,500-square-foot log home has six bedrooms and six baths and is just east of the Big Sky Resort. 


Red Feather Lodge | More
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Red Feather Lodge | More

When not skiing or boarding, guests can enjoy the home's amenities, which include a large dining area, game room with pool and shuffleboard, theater room, and hot tub. 

The Suncadia Sanctuary
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Suncadia Sanctuary

Cle Elum, Washington | Sleeps 22
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As well as an appealing name, this six-bedroom, eight-bathroom house offers incredible views of the surrounding forest, access to nearby Cle Elum Lake, and plenty of house amenities like ping pong, shuffleboard, walk-in showers, and a chef-friendly kitchen with a six-burner Wolf stove. 


The Suncadia Sanctuary | More
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Suncadia Sanctuary | More

Even better? It's within driving distance to tons of day trips, including Leavenworth, three ski resorts, and national and state parks. 

Mediterranean Mansion
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Mediterranean Mansion

Dallas | Sleeps 8 

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The Mediterranean milieus of Morocco or Croatia may be out this season, but this palatial getaway with lofty domed ceilings and five fireplaces for optimal coziness is tucked inside a quiet gated neighborhood just a few convenient miles from Dallas-Fort Worth International airport.


Mediterranean Mansion
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The Barn
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The Barn

La Pointe, Wisconsin | Sleeps 16

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This property was built from a 200-year-old Vermont hay barn disassembled, transported, and reassembled on 900 feet of private lakeshore. 

The Barn | More
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The Barn | More

It’s been featured on Martha Stewart Weddings and the Discovery Channel and is on beautiful Madeline Island.

The Santa Rosa Sound Home
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Santa Rosa Sound Home

Pensacola, Florida | Sleeps 30

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If you’re after a waterfront property, this home in Pensacola Florida may be perfect. With eight beds, eight baths, and lots of room for lounging and gathering, you and your party will be well taken care of.


Related: The 20 Best Beaches on the East Coast

The Santa Rosa Sound Home | More
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Santa Rosa Sound Home | More

The kitchen offers plenty of space for cooking a holiday meal. Other amenities include a pool, watercraft, and laundry room. 

The 1785 Inn
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1785 Inn

Intervale, New Hampshire | Sleeps 40

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Looking for a cozy New England setting? You’ll love this historic New Hampshire inn with stunning views of Mount Washington. 

The 1785 Inn | More
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1785 Inn | More

A few of the amenities: a fire pit, a hot pub, a 70-person dining room, and commercial kitchen.

The Lakefront Southern Plantation
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The Lakefront Southern Plantation | More
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The Georgian Lakefront | More

There’s a private dock, a 50-foot in-ground heated pool, outside sunken hot tub, a poolside fireplace for cooking and entertaining, and plenty of other amenities that will make your time there special. Don’t forget about the on-site canoes and kayaks if the weather is amenable.

Vista Verde
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Vista Verde | More
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Vista Verde | More

There’s a tennis court, a pool, and lots of room for you and your guests.

The Private Maine Beach
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The Private Maine Beach | More
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Private Maine Beach | More

There are six bedrooms, 15 beds, and the home sits on 2 acres with 300 feet of private sandy beach. 

The Orleans
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The Orleans

Chicago | Sleeps 16

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This historic, storefront brownstone includes four separate suites, each with its own kitchen. The group can gather on the rooftop patio, with a clear view of the John Hancock Center. There are bike rentals just outside the front door, and easy access to the El, as well as River North’s galleries and Lincoln Park.

The Orleans: More
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The Orleans: More

Throughout the building, rooms are warmed by exposed brick and brightened by modern art. Exposed ductwork adds to the industrial-chic appeal. Day and night views from the roof are Chicago at its best.


Related: Airbnbs That Put You in the Thick of Fall Foliage