Holiday rentals with a patio in Chatham

5 out of 5 average rating, 58 reviews

An open and cozy interior features a spacious bed dressed in soft linens, complemented by a seating area with a brown leather couch. A small dining nook with a black table and chairs is positioned near the entrance, allowing for natural light to brighten the room.

Tiny home in Brewster

Quaint & Cozy TinyHome! 300sqft/firepit/smallpetOK

⚓️PINCH OF SALT STUDIO COTTAGE⚓️ 🌹This romantic cottage offers a history all its own. Built in 1890 by a welder and his wife this tiny home is located within a small cottage community with 4 other dwellings-The Salty Doors! ❄️ minisplit A/C 🍴kitchenette 🧑‍🍳 basic cooking supplies 🛏️ queen bed (firm) 🚽 bathroom w/standup shower 🧼 Public Goods toiletries 🛌 cotton linens/down comforter 🍽️dining nook 📺 smart Roku TV 💫private patio 🔥 propane outdoor firepit 🌭 propane grill 🚿 outdoor open air shower

4.98 out of 5 average rating, 112 reviews

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.

Home in Harwich Port

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

4.89 out of 5 average rating, 117 reviews

A well-maintained garden features colorful flowers, including red poppies and purple lavender, set against a stone retaining wall. The cottage, visible in the background, includes a vibrant orange awning and an American flag flying above, surrounded by lush greenery.

Home in South Yarmouth

Cheerful, renovated 2 bdrm-block to beach. Dog ok.

ARTIST and AUTHOR'S Cape Cottage! Dog and Family Friendly-Cozy nautical decor. Located .2 miles from the beaches in South Yarmouth. Guests enjoy returning to "My Two Cents" aka "Poppie's Place"- a quintessential, cheerfully remodeled home surrounded by hydrangeas, roses, and colorful perennials. Tucked off Seaview Avenue on a private lane you will enjoy easy access to several beaches, shops, Captain Parker's, Skipper’s and other great restaurants, Pirate's Cove mini golf, museums, and arcades.

A charming cottage is seen from the front, featuring natural wood siding and a blue door. Well-maintained shrubs and blooming azaleas accentuate the entrance, while a stone pathway leads to the door, framed by a grassy area and trees in the background.

4.97 out of 5 average rating, 88 reviews

Serene Chatham cottage minutes from beach

Welcome to Cranberry Cottage, a 2 BR, 1 BA cottage centrally located & close to the best that Chatham has to offer. Perfect for couples or families! Situated at the end of a private street and overlooking a working cranberry bog, the house is surrounded by some of the Cape's best natural beauty and wildlife. The neighborhood offers walking paths to Ridgevale Beach (15-20 min; great for kids), conservation trails and the Cape Cod Rail Trail. By car, Ridgevale and Hardings Beaches are 5 min away.

4.96 out of 5 average rating, 121 reviews

A living room area presents a grey sofa adorned with patterned cushions, accompanied by a woven coffee table. A standing lamp provides light beside a simple side table with decor. The soft, green walls are complemented by dark curtains and framed artwork.

Home in South Yarmouth

Modern Beach & Pond Getaway | Heart of Cape Cod

Your perfect Cape Cod escape awaits! Coastal chic home base w/ king bed & AC near all Cape Cod has to offer. <8 min to pristine beaches, endless local shopping, entertainment & dining. Short walk to Wings Grove Beach to fish, kayak or swim in serene Long Pond - perfect for kids! Take in nature while biking the Cape Cod rail trail (4 min away) & ride all the way to the outer cape! BBQ, enjoy the firepit, fenced in yard, and outdoor shower. On cool nights, cozy up next to the indoor gas fireplace

4.89 out of 5 average rating, 105 reviews

A bright kitchen area is visible, featuring white cabinetry and modern appliances. A small dining table with two wooden stools is positioned near a window. The space is enhanced by natural light and wooden flooring, creating a welcoming atmosphere that connects to an adjoining living space.

Cottage in Dennis Port

Oyster Isle-Steps from the Beach!

A perfect seasonal escape, come enjoy the ocean waves and sunshine at this beach retreat! Spend time with family and friends exploring all the Cape has to offer in lively Dennis Port. Located steps from Haigas Beach, nearby playgrounds, ice cream shops, restaurants (Ocean House, Sandbar, Pelham House) and more. This 1 bedroom cottage comes fully equipped with a queen bed, beach essentials, outdoor shower, full kitchen & living space, A/C, parking, just steps from the beautiful Nantucket sound.

4.85 out of 5 average rating, 119 reviews

A charming white cottage is surrounded by a well-maintained grassy yard, featuring a stone walkway leading to the front door. The exterior is complemented by large windows adorned with shutters, and a light chimney is visible on the roof, adding to the welcoming curb appeal.

Cottage in Harwich Port

Cozy & Bright Cape Cod Cottage- Walk to the beach!

Come enjoy all the Cape has to offer in this peaceful and conveniently located home. Half-mile walk to the ocean! You'll be just five minutes away from both downtown Harwich Port and Dennis Port. Spectacular hiking and kayaking can be found right down the road at Bells Neck and Herring River. With a spacious yard that is perfect for relaxing and a cozy living area, this is the perfect coastal home away from home. The cottage is equipped with central A/C, speedy internet, and an outdoor shower.

4.93 out of 5 average rating, 113 reviews

A spacious outdoor area features a circular arrangement of colorful chairs, including blue, red, and green options. The inviting lawn is framed by trees, with a large glassed-in porch visible in the background, providing a seamless connection to the natural surroundings.

Home in Harwich Port

Stunning Home in Harwich Port

Welcome to our stunning retreat in charming Harwich Port! This beautiful 4-bed, 2-bath home is the perfect destination for your next getaway. The spacious interior and finished basement are perfect for families or groups and the big fenced-in yard is ideal for outdoor activities, relaxation and pets (please include pets when booking)! A 5 min drive from the beach and downtown, you'll enjoy all that the area has to offer. Book today and experience the best of Cape Cod in this beautiful home!

4.95 out of 5 average rating, 130 reviews

An aerial view captures a serene pond surrounded by lush greenery. Clear blue water reflects the sky, while sandy areas and aquatic plants line the edges. The tranquil environment suggests opportunities for relaxation and connection with nature.

Guesthouse in Brewster

Brand new, on a secret pond

Welcome to our chic guest house. This brand-new retreat includes a bedroom with king bed, a living room with a sofa bed, smart TV, sleek breakfast bar, and a contemporary bathroom with rainshower and a heated towel rail. Steps away the beach invites you to relax by the water of a semi-private pond next to the rail trail. Welcome to a retreat that strikes the perfect balance between contemporary luxury and the tranquility of nature – for those who appreciate the finer things in life.

4.89 out of 5 average rating, 106 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

5 out of 5 average rating, 64 reviews

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.

Holiday home in Chatham

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!

4.95 out of 5 average rating, 76 reviews

The renovated windmill exterior showcases unique architectural features with a pointed roof and prominent wooden blades. A bright blue door is framed by a brick pathway, leading to a garden of blooming daffodils, offering a cheerful first impression.

Cottage in Chatham

Renovated Chatham Windmill! Walk to Beach/Town!

Newly renovated Chatham Windmill! Beautiful Water View, Steps to Oyster Pond Beach & Main Street! Complete renovation of Windmill in 2022. This unique rental has one bedroom with king bed on second floor, with small full kitchen/dining area, two sitting/TV areas and full bathroom on first floor. Private patio with BBQ grill, dining table and chairs. Enjoy the beautiful water view from Adirondack chairs, just outside your door! Perfect spot for your vacation!

Popular amenities for Chatham Holiday Houses with Outdoor Verandahs

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

Apartment in North Eastham

A spacious living area features polished wooden flooring, with a cozy seating arrangement including two wicker chairs and a glass-top coffee table. Light streams in from a nearby window, illuminating a full-size refrigerator, induction cooktop, and a stacked washer and dryer in the background.

4.98 out of 5 average rating, 54 reviews

Billy & Beth's Bayside Lodging Cape Cod

Superhost

A single-story structure features weathered grey shingles and multiple windows allowing natural light. A small deck is present, accompanied by colorful chairs and a picnic table. Surrounding greenery adds to the outdoor space, providing a relaxed and inviting environment.

Apartment in Chatham

4.82 out of 5 average rating, 11 reviews

Studio in South Chatham

4.97 out of 5 average rating, 134 reviews

A private backyard features landscaped areas with green lawn and mulch, patio stones, and seating options. Comfortable blue chairs sit under an umbrella, adjacent to a wooden dining set. A fire pit area complements the space, surrounded by lush greenery and flowering plants.

Apartment in Plymouth

Downtown Backyard Oasis

4.99 out of 5 average rating, 84 reviews

The bedroom features a spacious bed framed by dark walls and two windows allowing natural light. Wooden flooring complements the warm tones, while two bedside lamps and a clothing rack with hangers add functionality. Potted plants enhance the inviting ambiance of the space.

Apartment in Sandwich

Clean private & cozy Cape Cod 1 br/ba with kitchen

5 out of 5 average rating, 67 reviews

The Brewster Book Store features a charming two-story structure with a dark shingle exterior. Large windows display colorful ice cream cone designs, creating a welcoming atmosphere. A sign above the entrance indicates the store name, while planters with flowers add a touch of greenery in front.

Apartment in Brewster

The Book Nook

Apartment in Hyannis Port

A modern kitchen area is presented, featuring white cabinetry and a countertop with seating for three. Natural light enters through multiple windows, illuminating the space. Essential appliances, including a microwave and coffee maker, are arranged neatly, alongside plants placed on shelves adding a touch of greenery.

5 out of 5 average rating, 34 reviews

Newly renovated apartment. Short walk to the beach

Superhost

A bright bedroom features blue walls and a floral accent wall. A spacious bed with a textured quilt is positioned prominently. Natural light enters through a skylight, and a flat-screen TV is mounted on the wall. Storage units in warm wood tones complement the space.

Apartment in Dennis Port

4.71 out of 5 average rating, 28 reviews

Pet Friendly King Suite in a great location

4.95 out of 5 average rating, 138 reviews

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

Apartment suite|Firepit|Private Deck|Pond Access

Holiday House Rentals with a Verandah

The exterior view of the house reveals a charming beach house design surrounded by lush greenery. A well-maintained lawn with various shrubs leads up to the entrance, while a clear blue sky enhances the serene setting. The home is situated amongst trees, providing a sense of privacy.

4.92 out of 5 average rating, 12 reviews

Modern Chatham Beach House

4.95 out of 5 average rating, 80 reviews

A spacious outdoor deck features comfortable, cushioned seating with a view of the ocean. A table is positioned centrally, inviting gatherings. The tranquility of the scene is enhanced by natural grass and the serene waters in the background, creating an ideal relaxing space.

Home in South Yarmouth

Oceanfront Vacation Home with Private Beach for 6

4.95 out of 5 average rating, 22 reviews

This charming home features a light-colored exterior with blue shutters and a welcoming door. A manicured lawn surrounds the property, showcasing lush green shrubs and colorful flower beds. Tall trees provide a natural backdrop, creating a peaceful and inviting setting.

Home in Harwich

Charming Cape Cod Retreat–Walk to Long Pond Beach!

4.97 out of 5 average rating, 29 reviews

An outdoor seating area is covered by a gazebo, featuring plush blue cushions on woven furniture. A fire pit table sits at the center, with flames providing warmth. Beyond the seating, a fenced-in lawn creates a private retreat, complemented by a storage shed.

Home in Dennis Port

3-min walk to BEACH! Private luxury Backyard!

The exterior of a recently renovated house is shown, featuring blue siding and white trim. Two symmetrical green shrubs accompany the entrance, which has a red door adorned with a decorative wreath. Windows with red shutters provide a balanced look to the facade.

4.98 out of 5 average rating, 43 reviews

Chatham House Close to Beaches and Bike Path.

The cottage is nestled among trees, displaying a classic shingle exterior. A welcoming screened-in porch with multiple windows provides natural light. The landscaped yard features greenery and flower beds, along with a set of wooden steps leading up to the home.

4.96 out of 5 average rating, 48 reviews

Chatham Beach Cottage 2BR - 5 min walk to beach

A spacious living area features high ceilings and large windows, creating an open atmosphere. A comfortable arrangement of sofas and armchairs provides ample seating. A fireplace with a decorative mantel is situated against a soft blue wall, complemented by a natural woven coffee table.

5 out of 5 average rating, 25 reviews

Beautiful, Calm, and Quiet Retreat in Chatham

5 out of 5 average rating, 56 reviews

Home in South Dennis

Family Retreat in the Heart of Cape Cod!

Holiday condos with a patio

5 out of 5 average rating, 50 reviews

An open-concept interior features a dining area with a table and four chairs, leading to a cozy living space with a sofa and television. A staircase is visible, enhancing the airy feel. Large windows allow natural light to illuminate the neutral-toned décor.

Condo in Chatham

Condo on Lighthouse Beach in Chatham

The exterior of the Cape Cod-style house displays distinctive shingles and white trim. Large windows are framed symmetrically, allowing natural light to enter. A fenced area is visible in the front, with a walkway leading to the entrance. The scene is set against a clear sky.

5 out of 5 average rating, 33 reviews

West End: 2-Bed Condo w/ Private Patio & Parking

A cozy studio is highlighted by a spacious queen bed with decorative pillows and a white coverlet. Framed art featuring sailing imagery adorns the walls. A small sofa is positioned nearby, while a kitchenette and dining area are visible in the background.

4.97 out of 5 average rating, 161 reviews

Downtown Condo with Dedicated Parking

A light-filled living area features large windows that overlook the water, allowing for panoramic views. The room is furnished with a cozy sectional sofa, two armchairs, and a wooden dining table surrounded by pink chairs. Decorative elements include ocean-themed wall art and warm wood accents.

4.98 out of 5 average rating, 65 reviews

Stunning 2Bd/2Ba waterfront condo w/ beach access!

4.97 out of 5 average rating, 58 reviews

A sandy pathway leads through gentle dunes to the beach, where the ocean horizon meets a sky filled with soft clouds. Green grasses frame the scene, creating a serene transition to the water.

Condo in Harwich Port

Door to shore in a hop, skip, and a jump!

A bright dining area features a round table surrounded by five chairs with blue and white patterns. A large pendant light hangs above, and natural light enters through two windows. Decorative plates adorn the wall, complemented by a circular mirror and an accent vase.

5 out of 5 average rating, 93 reviews

Perfect west end location! 1 bd/parking