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Vacation rentals with outdoor seating in Chatham

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Top-rated outdoor seating rentals in Chatham

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A bright bedroom showcases a spacious bed with white linens and decorative pillows. A wooden dresser and bedside tables are positioned nearby. Nautical-themed decor, including a wall sign and a decorative ship's wheel, enhances the coastal ambiance. Natural light enters through a window overlooking the peaceful surroundings.

Home in Chatham

4.94 out of 5 average rating, 127 reviews

Walk to Ridgevale Beach

We have done extensive renovation and remodeling to the home with attention to detail. We believe we have created a warm and inviting atomosphere. The home is decorated in a coastal style with carefully chosen accents from the edison bulbs in the dining area to the custom barn/boathouse style door and repurposed hand hewn 18th century beam that anchors the staircase. The Kitchen is equipped with the same attention to detail for those who enjoy preparing their own meals. Summerfell is an entire home rental. Both hosts live nearby, Patty and Bill will be accessible via cell, text and email. The property is in a peaceful neighborhood with a good mix of seasonal homes and full time residences. The area has a number of quiet roads perfect for evening strolls. Of course, the beach is a short 5 minute walk away. The kitchen is equipped for the guest who enjoys cooking. From small appliances (Crockpot, waffle iron, blender, hand mixer etc) to small gadgets (citrus press, microplane, garlic press, potato ricer etc) A three burner weber gas grill is on the deck.

The stylish cottage features a classic shingle exterior with blue shutters and a welcoming front porch. Lush green shrubbery and well-maintained landscaping complement the home's curb appeal. The clear blue sky adds to the inviting presence of the cottage, enhancing its charming character.

Cottage in Chatham

5 out of 5 average rating, 35 reviews

"Escape Hatch' Chatham, In town Location

Stylish Chatham Cottage, 2 min walk to Main St, enjoy picnics on Chase Park, delightful Windmill is located steps away! Walk or cycle to the beach! Bright clean and stylish cottage with fresh linens & towels for your use! Deck chairs, beach toys and fully fenced bluestone patio yard! Ideal for little ones.3 bedrooms (Room #1 downstairs -full, Second floor :Room #2 Queen Bed, Room # 3 has two twins) 1 & 1/2 bath with a darling kitchen. OUTDOOR SHOWER! Summer Rental is Saturday to Saturday.

Top guest favorite

A serene waterfront scene features lush greenery and blooming hydrangeas in shades of blue and green. A calm pond reflects the surrounding trees, with a wooden dock extending into the water. The area appears tranquil, inviting relaxation and connection with nature.

Guest suite in Chatham

4.99 out of 5 average rating, 241 reviews

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table just steps to a fresh water pond & outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to downtown Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

A spacious roof deck features a dining table with seating for eight, shaded by a vibrant red umbrella. A lounge area showcases comfortable seating against a backdrop of a beautiful sunset. A grill and a cornhole game add to the outdoor enjoyment.

Home in Chatham

5 out of 5 average rating, 9 reviews

Luxury Home- Chatham Center- Walk to Town + Beach

Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is perfect for families, couples, or a group of friends looking to be walking distance to restaurants, boutiques, the beach & so much more! Enjoy an extremely spacious home with almost 2,700 sq ft of living space, 3 ensuites, & a large roof deck. In Downtown Chatham .3 Miles to Oyster Pond .5 Miles to Seaside Links Golf Course Experience Chatham with us & learn more below!

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

Home in Chatham

4.95 out of 5 average rating, 282 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Top guest favorite

The exterior of a spacious house is shown, featuring a large front porch with a gentle slope and decorative flowers. An attached garage is visible, and the well-manicured lawn surrounds the property. A private gravel driveway leads to the entrance, shaded by trees under a clear blue sky.

Guest suite in Chatham

4.99 out of 5 average rating, 121 reviews

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

Top guest favorite

A hammock is stretched between two trees in a lush garden area, surrounded by vibrant green grass and a variety of shrubs and trees. Flower pots adorned with colorful blooms add a touch of charm to the peaceful outdoor space.

Guest suite in East Harwich

4.99 out of 5 average rating, 608 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Top guest favorite

A gravel driveway curves through lush landscaping leading to a charming home set among tall trees. A large rock with a number '8' is positioned prominently near the path, providing clear identification of the property. The scene is tranquil and inviting.

Apartment in Chatham

4.97 out of 5 average rating, 264 reviews

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

A cozy cottage is framed by tall trees, showcasing a landscaped yard with a mix of grass and small shrubs. The home features a light-colored exterior with dark shutters and a welcoming front porch with steps leading up to the entrance.

Cottage in Chatham

4.94 out of 5 average rating, 173 reviews

Cape Cod Classic Cottage Near Forest Beach

See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

The bathroom features a freestanding white soaking tub with a wooden shelf holding toiletries and a glass of wine. A textured blue throw is draped over the side, and a light blue mat with the word 'PEACH' adds a touch of color.

Apartment in Brewster

4.96 out of 5 average rating, 163 reviews

Sophisticated, Private Cape Cod living

LOCATION: 3/4 mile off main road (unpaved road). Located on the town line of Brewster and Orleans with less than 5 minutes to Chatham or Harwich by car. Nauset and Skaket beaches are less than 3 miles away. Nickerson state park less than 1 mile away. Cape Cod National seashore is located within 7.2 miles of our property. Shopping on Main Street in Chatham is 15 minutes. Enjoy a nice, tranquil walk, listen to the birds or feast your eyes on the surrounding conservation land.

Top guest favorite

An open concept living area features a comfortable white couch and armchair, with a wooden coffee table at the center. The kitchen, visible in the background, is well-equipped and includes a fridge, while a dining area with two stools is highlighted. Natural light brightens the space.

Vacation home in Chatham

5 out of 5 average rating, 50 reviews

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

An open-concept living area features a spacious blue sectional sofa and a flat-screen TV mounted on the wall. Natural light floods the room through large windows, offering views of the surrounding greenery. A decorative plant and a textured area rug add warmth to the space.

Condo in Chatham

4.87 out of 5 average rating, 105 reviews

Steps to Private Beach in Chatham

2 Bedroom condo with views of the beach, ocean and marina. This wonderful condo is part of a beachfront/oceanfront complex, with steps to your own private beach in Chatham! We are within a mile of beautiful downtown Chatham and within a short walk to Chatham’s famous lighthouse beach and Monomoy Wildlife refuge. Whether by land or sea, there's something for everyone. This is a great place to make memories.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Chatham outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Top guest favorite

A comfortable outdoor seating area sits on a patio overlooking a serene lake. Warm sunlight highlights the soft cushions of the wicker chair, which is paired with a decorative pillow. Lush greenery and gentle ripples on the water create a peaceful backdrop.

Home in Harwich

4.94 out of 5 average rating, 47 reviews

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

Top guest favorite

A serene outdoor seating area is set by the waterfront, featuring two chairs with teal cushions and a white table. Lush greenery surrounds the area, enhancing the view of the calm waters and trees beyond. Lanterns add a subtle decorative touch to the space.

Home in Yarmouth Port

4.99 out of 5 average rating, 352 reviews

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

A spacious dining area features a large wooden table surrounded by dark chairs, complemented by a decorative centerpiece of fresh flowers. Natural light streams in from windows, illuminating the room, while a cozy living area is visible through the open doorway.

Home in Chatham

4.96 out of 5 average rating, 26 reviews

Main St fun for groups! Game barn! Walk to town!

Top guest favorite

A bright and airy living space features a wooden chair and a glass table surrounded by colorful chairs adorned with floral patterns. Natural light floods in through the windows, highlighting the seaside decor and vibrant mosaic backsplash in the background.

Home in Yarmouth Port

5 out of 5 average rating, 69 reviews

Beachfront· Sauna· Screened Patio· 2Kings· DogsYes

A charming two-story Cape house is shown, with a light blue vehicle parked on a gravel driveway. American flags hang from the windows, surrounded by mature trees and landscaping. The property features a welcoming entrance and a view of the adjacent structure.

Home in Chatham

4.87 out of 5 average rating, 15 reviews

Jean's Dream - Renovated Chatham House

A wooden dock extends into a serene freshwater pond, surrounded by lush green foliage. The calm water reflects the clear blue sky and distant tree line, creating a tranquil setting for relaxation and outdoor activities.

Home in Brewster

4.87 out of 5 average rating, 211 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

A modern kitchen features white cabinetry and stainless steel appliances. A large island with seating for two is positioned next to a dining table with light wood chairs. Natural light fills the space through sliding glass doors leading to the outdoor area.

Home in Chatham

4.97 out of 5 average rating, 103 reviews

Chatham Charm

An outdoor paver patio is equipped with a dining table and chairs, illuminated by string lights overhead. A green umbrella provides shade, and a Weber grill sits nearby. Beyond the patio, a spacious yard is surrounded by trees, offering a tranquil atmosphere.

Home in Chatham

4.95 out of 5 average rating, 22 reviews

Close to Beach Renovated Dog Friendly Cape Cottage

Apartment rentals with outdoor seating

Top guest favorite

A charming studio cottage with wooden shingles is nestled among trees, featuring a private deck and gas grill. Colorful flowers line the pathway leading to the entrance. A lush green lawn surrounds the building, creating a tranquil outdoor setting.

Apartment in Brewster

4.96 out of 5 average rating, 108 reviews

Songbird Studio- Secluded but close to everything!

The exterior of the cozy residence is highlighted by a welcoming porch, featuring a combination of natural stone and bricks. Lush greenery surrounds the area, and a wooden lattice adorned with flowers adds charm. Sunlight filters through the trees, illuminating the inviting entrance.

Apartment in North Eastham

4.91 out of 5 average rating, 272 reviews

Eastham Escape

Top guest favorite

A modern kitchen is showcased, featuring navy blue cabinetry and wooden countertops. Equipped with a stainless steel refrigerator, oven, and a farmhouse sink, the space includes a toaster and coffee maker. Shelves display dishware, while bright light enhances the welcoming atmosphere.

Apartment in Mattapoisett

4.98 out of 5 average rating, 107 reviews

Brand new! Whole apartment, huge tub, full kitchen

A serene beach landscape stretches under a clear blue sky, with soft sandy shores meeting calm waters. A small sailboat rests on the sand, surrounded by lush green shrubs and trees in the distance, enhancing the natural beauty of the coastal environment.

Apartment in South Orleans

4.93 out of 5 average rating, 135 reviews

Walk to private beach, spacious peaceful apartment

A cozy studio apartment features sloped ceilings and natural light filtering through a window. A spacious bed is positioned against the wall, with decorative pillows and a woven rug adding texture. Shelves hold books and playful aquatic-themed decor enhances the serene atmosphere.

Apartment in East Orleans

4.95 out of 5 average rating, 295 reviews

Cozy Waterfront Apartment, Private Beach Access

A spacious bedroom features a four-poster bed with a light bedding set, complemented by two large, round ottomans. A patterned wall adds texture, while a cozy seating area is visible in the background. Soft lighting enhances the calm ambiance.

Apartment in Dennis Port

4.97 out of 5 average rating, 107 reviews

Apartment suite|pond access|Firepit|Private Deck

An open living area features light wood flooring with a large window allowing natural light. A comfortable couch is situated near a wooden coffee table. A dining table with chairs is visible, along with a well-equipped kitchen adorned with modern appliances.

Apartment in Brewster

4.83 out of 5 average rating, 118 reviews

A quiet, private, unique spot in a great location!

Top guest favorite

A cozy living area features a green sofa adorned with a patterned throw pillow. A decorative ottoman complements the space, while soft lighting is provided by a bedside lamp on a nearby table. Coastal-themed artwork is displayed on the walls, enhancing the relaxed ambiance.

Apartment in Wellfleet

4.84 out of 5 average rating, 363 reviews

Beach Plum Apt w/Private Deck & BnB Hot Tub Access

Condo rentals with outdoor seating

A modern kitchen features sleek white cabinetry and a bar area with two high-backed stools. Pendant lights hang above the bar, illuminating a tray with decorative items. The space is arranged for convenience, showcasing well-organized counters and appliances.

Condo in Provincetown

4.92 out of 5 average rating, 292 reviews

Modern Provincetown Condo.

A cozy living area is featured, furnished with a plush navy sectional sofa adorned with decorative pillows. A stylish coffee table sits in front, accompanied by a glass side table. A flat-screen TV is mounted on the wall, and light enters through the nearby window.

Condo in Provincetown

4.88 out of 5 average rating, 154 reviews

Serene, Light-filled Loft

A welcoming entryway is observed, featuring a rustic 'WELCOME' sign on the wall. Light wood flooring extends into a cozy living and dining space, illuminated by natural light. A dining table is visible in the background, surrounded by comfortable chairs.

Condo in Brewster

4.97 out of 5 average rating, 180 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

A charming exterior view of a two-story Cape Cod building is presented, framed by well-maintained greenery and colorful flowers. A white picket fence borders the entrance, which features stairs leading up to a welcoming porch adorned with umbrellas and seating.

Condo in Provincetown

4.8 out of 5 average rating, 318 reviews

Best location in Ptown,1 Bedroom,PARKING/WaterVIEW

The living area features a dark sofa and light wood flooring. Large glass doors open onto a private deck with water views. Two outdoor chairs are positioned on the deck. Bright artwork adorns the walls, complemented by natural light from the windows.

Condo in Provincetown

4.93 out of 5 average rating, 156 reviews

Westend Waterfront Luxury Condo-Provincetown

A cozy living area is furnished with a comfortable sofa and a wooden coffee table. A television is mounted on the wall above a white fireplace. Natural light streams through skylights, enhancing the airy atmosphere. A soft rug grounds the space, adding warmth.

Condo in Provincetown

4.92 out of 5 average rating, 195 reviews

West End Cozy, Bright and Airy!

A serene view from a private deck is presented, showcasing the expansive bay beyond. Two lounge chairs with blue and white striped cushions are positioned for relaxation, while the manicured lawn and beach area are visible, inviting guests to enjoy the outdoor space.

Condo in Provincetown

4.89 out of 5 average rating, 187 reviews

Bayshore 2:Direct waterfront/Parking/Pets welcome

Top guest favorite

A cozy living area features a dark sofa with patterned cushions and a green accent pillow. A low table holds a remote and a decorative item. A wall-mounted TV displays a program, while framed black-and-white photographs adorn the adjacent wall, complemented by light streaming through partially closed window shutters.

Condo in Provincetown

4.94 out of 5 average rating, 127 reviews

ALL ABOUT LOCATION INCLUDING PARKING!

Quick stats about vacation rentals with outdoor seating in Chatham

Total rentals
260 properties
Nightly prices starting at
€ 51 before taxes and fees
Total number of reviews
9.1K reviews
Family-friendly rentals
230 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
10 properties have a pool

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