Vacation rentals with outdoor seating in Chatham

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

4.98 out of 5 average rating, 120 reviews

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

A spacious living area features a light grey sectional sofa adorned with blue and white throw pillows. A rustic wooden coffee table is positioned on a woven rug, while an entertainment unit holds a television. Natural light fills the room through two large windows.

5 out of 5 average rating, 107 reviews

PTown Harbor & Beach Side 1 Br Condo & Deck!

Recently renovated in 2019 and located in the heart of Provincetown our large 1 bed condo is just a 7 min walk from the ferry and right by most parking lots. Bright & open space, clean lines in the kitchen/living room, with very large bedroom and true full sized bathroom. We have an exclusive use, furnished large deck with gorgeous bay views of MacMillan Pier and even the Monument. Working from home? We have a dedicated setup. There's direct access to the beach just steps away via the courtyard!

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.

4.96 out of 5 average rating, 312 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.

4.95 out of 5 average rating, 114 reviews

An open living area is highlighted by vaulted ceilings and large windows that allow natural light to illuminate the space. A comfortable seating arrangement faces a coffee table, while a dining area with bar stools is situated near the kitchen. A spiral staircase leads to the upper level.

Guest suite in Plymouth

Manomet Boathouse Station #31

The Boathouse was a part of the Manomet Coast Guard Station on Manomet Point. When the station was decommissioned and eventually dismantled, the Boathouse was moved and attached to our home as a separate space. Guests will have full and private access to this beautiful and spacious 1,800 square foot home with 11 foot vaulted ceilings and antique southern exposure windows. The open first floor has a living room, kitchen, pool table and bathroom. A spiral staircase leads to the bedroom.

4.99 out of 5 average rating, 132 reviews

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

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.

4.99 out of 5 average rating, 651 reviews

A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.

Guest suite in Harwich

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.

A charming beach house with shingle-style siding is displayed, set within a landscaped yard. Two large bushes frame the entryway, and the building features multiple rooflines and skylights. A brick pathway leads to the front door, with trees providing partial shade in the foreground.

4.96 out of 5 average rating, 113 reviews

Beachfront Charmer! Newly Renovated.

Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

4.88 out of 5 average rating, 110 reviews

The kitchen features white cabinetry and stainless steel appliances, with a large granite island equipped with seating. Natural light floods in from the adjoining dining area, enhanced by multiple windows that offer views of the surrounding greenery.

Condo in Chatham

Walk to beach! Chatham Luxury near downtown, CBI!

Chatham Searenity! BEACH ACCESS! Walk to beautiful beach overlooking monomoy! 2 minutes from Chatham Bars Inn, Chatham links golf & downtown! Luxury 2 bedroom, 2 bath condo with full kitchen & cookware. Quiet, comfy space centrally located. Peaceful, relaxing private space with large queen bed, daybed w/ pull out trundle, A/C, washer dryer, Wifi & ample parking. Hulu live tv, Netflix, Prime video, HBO max, Disney+. Central to everything! Perfect Cape escape. IG @chatham_searenity

A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

4.97 out of 5 average rating, 171 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

A modern kitchen features stainless steel appliances and a tiled backsplash, with a clear view of the adjoining dining area. Soft overhead lighting illuminates the space, complemented by hardwood flooring. A large window allows natural light to enhance the inviting atmosphere.

4.95 out of 5 average rating, 100 reviews

Spacious Pet Friendly Cape, Large Yard

Our home is located in a quiet neighborhood close to beaches, golf courses and bike trails. It is a short drive to Chatham town center and is the perfect location to be close to all attractions but secluded enough to unwind. Take advantage of the outdoors on a new deck and large backyard. Large, mature plants and trees surround the property on three sides. Blackberry, raspberry and blueberry bushes in the backyard provide ripe fruit in the summer months.

4.97 out of 5 average rating, 230 reviews

A shaded patio area is framed by a white pergola adorned with blooming wisteria. A wicker loveseat with floral cushions and a matching lounge chair are positioned along the paved surface, creating a relaxing outdoor space surrounded by greenery.

Guesthouse in Yarmouth

“The Pink Cottage” in Historic South Yarmouth

“The Pink Cottage” is a charming one-bedroom private building nestled into a beautiful historic property in South Yarmouth. Enter through the pergola patio, enjoy a spacious living space with dining and kitchen area. The one-bedroom with large closet is comfortably outfitted with all linen necessities, full bath with stand-up shower. Outdoor shower just off the patio, grill and more! Very quiet and private.

A serene view of a calm harbor filled with various boats, all anchored in the water. The foreground features a grassy area with a wooden path leading toward the water's edge, while vibrant greenery and flowers are visible along the border.

4.97 out of 5 average rating, 102 reviews

Oceanfront Chatham Village Home

Quiet Peaceful Oceanfront Home, Short Walk to Chatham Village and Walk to Lighthouse Beach. Sleeps 12. Large kitchen, stainless steel appliances, gas stove. Every Room except one room has amazing ocean views! Stone patio overlooks Ocean Harbor on Little Mill Pond. A Video Walkthrough of the house, featured by Eileen Cotter of Pure Wander: https://www.youtube.com/watch?v=_tqi6m8-1zs&t

Popular amenities for Chatham outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

Superhost

Home in Eastham

5 out of 5 average rating, 5 reviews

10 min walk to Beach - Amazing View & Huge Deck

A dining area features a light-colored table adorned with a floral centerpiece and a decorative sailboat. White chairs surround the table, which is set against a backdrop of a softly-lit, inviting space. A glimpse of a living room is visible through the framed opening.

4.94 out of 5 average rating, 49 reviews

Relaxing Harwich retreat with beautiful back yard

4.93 out of 5 average rating, 128 reviews

A spacious deck features two wooden Adirondack chairs facing a serene waterfront view of Vineyard Sound. Lush greenery surrounds the area, and the calm water reflects the soft hues of the sky, creating a peaceful outdoor setting.

Home in Woods Hole

Juniper Point Cottage With Ocean View

5 out of 5 average rating, 235 reviews

A charming colonial home is framed by vibrant yellow blooms. The front porch features a welcoming entrance with a dark door and white trim, flanked by two large windows. Lush greenery surrounds the property, creating a serene atmosphere.

Home in Harwich Port

Harwich Retreat on Cape Cod - Relax or explore!

A modern kitchen is presented, featuring stainless steel appliances and sleek cabinetry. A skylight allows natural light to fill the space. The countertops are finished in a light tone, complemented by a neutral backsplash. A window offers a view of the outdoors.

4.92 out of 5 average rating, 26 reviews

7th Vacation in Harwich

Superhost

5 out of 5 average rating, 4 reviews

Cape Cod Historical Oasis | Mecarta Farm

4.99 out of 5 average rating, 67 reviews

Thinking of Summer Already? - Book Now Summer '26

A charming cottage is framed by tall white pine trees, providing shade and privacy. The exterior features light-colored siding and blue shutters. Seating options include two outdoor chairs positioned on the ground amidst pine needles. A screened-in porch is visible on the right side of the building.

4.88 out of 5 average rating, 41 reviews

Chatham cottage w/ laundry & AC! Walk to beach!

Apartment rentals with outdoor seating

Apartment in Sagamore Beach

A bright living area features a large window that allows natural light to fill the space. Comfortable seating includes a gray sofa and a dark blue loveseat. A wooden coffee table sits between them, and a ceiling fan helps maintain a comfortable temperature.

4.98 out of 5 average rating, 123 reviews

Cape Cod Canal Home

4.97 out of 5 average rating, 127 reviews

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

Songbird Studio- Secluded but close to everything!

4.9 out of 5 average rating, 122 reviews

An outdoor seating area is presented with a round table and four chairs, shaded by a vibrant red umbrella. A decorative wall hanging and plants add character to the wooden exterior. A surfboard rests against the wall beside the entrance, surrounded by stone and greenery.

Apartment in Eastham

Peaceful retreat in the woods...

Apartment in South Orleans

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.

4.93 out of 5 average rating, 141 reviews

Walk to private beach, spacious peaceful apartment

4.96 out of 5 average rating, 283 reviews

A rustic, two-story cabin is surrounded by lush landscaping. A green door welcomes visitors, while a small stone pathway leads to a pair of outdoor chairs situated on a grassy lawn. The harmonious design includes natural stone walls and shaded trees.

Apartment in Chatham

The Knoll

Apartment in East Orleans

A sandy path meanders through tall grass, leading toward a tranquil sunset in the background. The sun casts a warm glow over the horizon, suggesting the evening calm of the beach area. Soft greens and earthy tones create a peaceful natural setting.

4.95 out of 5 average rating, 321 reviews

Cozy Waterfront Apartment, Private Beach Access

Apartment in North Falmouth

A comfortable living room features a floral-patterned couch and a plush armchair, arranged around a wooden coffee table. Natural light pours in through a large bay window, enhancing the light-colored walls. Two decorative lamps add soft illumination, while framed pictures adorn the wall.

4.94 out of 5 average rating, 309 reviews

Upscale suite w/ separate entrance.

4.84 out of 5 average rating, 135 reviews

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

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

Condo rentals with outdoor seating

Superhost

A serene waterfront view showcases a calm pond surrounded by trees in autumn colors. An inviting sandy beach area features bright blue adirondack chairs and a kayak resting on the shore, reflecting a peaceful outdoor setting.

Condo in Plymouth

4.77 out of 5 average rating, 163 reviews

Clear Pond Pet Friendly Retreat

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.

4.93 out of 5 average rating, 327 reviews

Modern Provincetown Condo.

4.97 out of 5 average rating, 198 reviews

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

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.

4.8 out of 5 average rating, 372 reviews

Best location in Ptown,1 Bedroom,PARKING/WaterVIEW

A bright living space features large windows providing views of the waterfront. A white sofa and a cozy sitting area surround a circular coffee table. A patterned area rug anchors the space, while light filters in, enhancing the serene atmosphere.

4.99 out of 5 average rating, 110 reviews

Modern Beachfront Condo, Great Views and Location!

4.88 out of 5 average rating, 128 reviews

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

Private Beach in Chatham - Sleeps 5

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.

4.95 out of 5 average rating, 137 reviews

ALL ABOUT LOCATION INCLUDING PARKING!

A spacious dining area is presented with a modern table surrounded by six white chairs. Natural light enters through multiple windows, illuminating the comfortable gray sofa and sleek entertainment unit in the background, which features a minimalist fireplace.