Cottage holiday rentals in Chatham

Cottage in South Yarmouth

A view of the waterfront shows a relaxing outdoor seating area featuring a coffee table and comfortable gray sofas. Lush greenery and blooming hydrangeas surround the space, while a clear lake reflects the sky in the background.

5 out of 5 average rating, 240 reviews

SerenityViews | Lakefront | KingBed | Kayaks | FPL

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!

4.98 out of 5 average rating, 205 reviews

A serene view of a crystal clear pond is framed by lush trees. The calm water reflects the blue sky and scattered clouds, creating a tranquil atmosphere. A wooden pathway leads to the water's edge, inviting exploration and relaxation.

Cottage in Dennis

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

A cozy living room features a large, light-colored sectional sofa adorned with various decorative pillows. A neutral coffee table sits centrally on a woven area rug. Natural light enters through multiple windows, and a wall-mounted flat-screen TV is visible, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 272 reviews

Walk to Beach - Experience Dennis Beach House - AC

A quaint, cozy, well-decorated & well-equipped Cape Cod cottage located .2 miles away from Sea St Beach and a variety of other bars/restaurants, coffee shops and more. The house sleeps 5 people comfortably and has 1 small bathroom. Kitchen is fully stocked. 4-6 bath towels will be provided. The house has many smart home tech amenities, central air, Temperpedic mattresses, and a lovely & large outdoor space/back deck. First time booking on Airbnb? Save using link: www.airbnb.com/c/brianm30025

4.97 out of 5 average rating, 268 reviews

A charming cottage with a shingle exterior is framed by a vibrant yard. A white picket fence encloses flower beds, and a small patio features an umbrella for shade. A welcoming pathway leads to the front door, surrounded by greenery and a manicured lawn.

Cottage in Chatham

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property.

4.95 out of 5 average rating, 383 reviews

A charming single-story home is presented with light grey shingles and dark blue shutters. A paved pathway leads to the front door, framed by manicured green lawns and landscaped flower beds. Trees and shrubs add to the serene outdoor environment.

Cottage in Harwich Port

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

4.98 out of 5 average rating, 313 reviews

A cozy living space features a striped sofa and a round table set near a rug. Light from the windows brightens the room, which leads to a bedroom visible in the background, adorned with a patterned quilt and vibrant pillows.

Cottage in Pocasset

Upper Cape Cozy Cottage

Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.

4.95 out of 5 average rating, 258 reviews

A serene dock extends over calm waters, featuring two Adirondack chairs positioned beside vibrant potted flowers. Lush greenery frames the scene, providing a peaceful backdrop for relaxation. The setting invites guests to unwind and enjoy the tranquility of the freshwater pond.

Cottage in Eastham

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor showers, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.

4.93 out of 5 average rating, 186 reviews

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

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 cottage's exterior features a welcoming entrance with a white door and blue shutters. A well-maintained lawn stretches in front, bordered by a gravel path. Two Adirondack chairs are positioned on the lawn, inviting relaxation under the clear blue sky.

5 out of 5 average rating, 118 reviews

@TheCapeSummerHouse - 2bdrm Cottage in Dennisport

Explore Cape Cod from a Beautiful Cottage in Dennisport Village Freshly updated and sunny! This cozy cottage exudes coastal charm. It has a large yard perfect for the kids to play & located just .2 miles to Glendon Beach on Nantucket Sound. It’s a great place to get away for a Cape Cod vacation: central AC, fenced-in backyard with a Weber gas Grill & fire-pit, quintessential outdoor shower, WiFi, Smart TV’s, updated kitchen including a dishwasher, washer & dryer.

4.92 out of 5 average rating, 237 reviews

The cottage's exterior is framed by lush greenery, featuring a spacious deck with a large blue umbrella and picnic table. Vibrant flower pots add color, while stepping stones lead towards the entrance, inviting guests to enjoy the peaceful surroundings.

Cottage in North Eastham

Classic Cape Cod Cottage

No cleaning fee! 15 min walk to the best bayside beach, Thumpertown Beach. The cottage is in a very peaceful wooded setting. A beautiful, charming 2 bedroom cottage 15 min walk to Thumpertown Beach. It's situated on a triple sized lot, close to the outer Cape's favorite attractions. Eastham is known as the Gateway to the Cape Cod National Seashore. Please note, from June 13 to September 6 we have a 7 night minimum from Saturday to Saturday.

4.93 out of 5 average rating, 109 reviews

The exterior of a charming cottage is displayed, featuring a brick chimney and light-colored shingles. Lush greenery surrounds the property, complemented by two blue planters near the entrance. A stone pathway leads to the door, and a picnic table is visible on the adjacent patio.

Cottage in North Truro

Unique Waterfront Artist Cottage

Once a horse stable, Lil Rose now sleeps up to five just a short walk from a private beach. PLEASE READ BEFORE BOOKING: Rentals in season (April-October) are only offered by the week (Saturday-Saturday). November rentals are offered with a 4-night minimum. Rentals December-March are offered with a 3-night minimum. Pets are accepted (max 2) but you MUST let us know in your booking request about your pet so that we can prepare the property.

4.86 out of 5 average rating, 556 reviews

An open living area features a comfortable gray sofa facing a round dining table and chairs. A full kitchen is equipped with modern appliances, including a stainless steel refrigerator. Natural light brightens the space through large windows, complemented by light-colored wooden flooring.

Cottage in South Dennis

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Popular amenities for Chatham cottage rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.92 out of 5 average rating, 286 reviews

The cottage, surrounded by mature landscaping, is located near a private beach. A sandy expanse is visible in the background, highlighting the close proximity to the shore. Nearby structures exhibit a rustic charm, contributing to the serene beach environment.

Cottage in East Sandwich

Hideout at Water's Edge, 131 North Shore Blvd, #4

The open kitchen features modern cabinetry with ample storage and stainless steel appliances. A large island with bar seating is complemented by a dining area. Natural light fills the space through a nearby door leading to the outdoor area.

5 out of 5 average rating, 10 reviews

Willows Main House

A shaded outdoor dining area is present, featuring a red patterned tablecloth over a circular table. Two white chairs are positioned alongside the table, with a striped umbrella providing protection from the sun. A grassy yard and wooden fencing serve as the backdrop.

4.79 out of 5 average rating, 87 reviews

Best Little Beach Cottage!

The charming exterior of the cottage is surrounded by lush greenery and features a welcoming path made of pavers. Two large windows flank the entrance, while the quaint door is framed by warm wood shingles, enhancing the serene atmosphere.

4.93 out of 5 average rating, 28 reviews

NEW! East End Cottage with Private Hot Tub!

4.97 out of 5 average rating, 133 reviews

Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.

Cottage in South Dennis

Local Beach+ Fireplace + Hot Tub Under the *Stars*

4.88 out of 5 average rating, 33 reviews

A view from the dock extends across the calm water of Sand Pond, with lush trees lining the opposite shore. The clear blue sky is reflected in the water, creating a tranquil atmosphere. Two wooden posts stand towards the edge of the dock.

Cottage in Harwich

Lakeside Waterfront House in Harwich: 4+beds, 3bth

4.7 out of 5 average rating, 44 reviews

The exterior of the house is viewed from the shore, featuring a grassy area with purple loungers positioned by the water. The house, with its light-coloured siding and multiple windows, overlooks a calm pond surrounded by trees and nearby residences.

Cottage in Onset

The Crab House @ The OBC Beach Resort and Habitat

4.87 out of 5 average rating, 38 reviews

An outdoor area features white Adirondack chairs arranged around a stone fire pit, filled with firewood. The scene overlooks a calm river lined with trees, under a clear blue sky. A boat is visible in the distance, enhancing the waterfront view.

Cottage in Mashpee

The Front Cottage: Waterfront/Dock/Hot tub

Pet-friendly cottage rentals

4.97 out of 5 average rating, 256 reviews

Cottage in Sagamore

Beach Cottage, without going over bridges to Cape!

A charming cottage features a front yard with a well-maintained garden. A white picket fence encloses the area, while lush greenery and colorful flowers contribute to a vibrant exterior. The extended bay window allows ample natural light, complementing the inviting entrance.

4.81 out of 5 average rating, 493 reviews

Private cottage green friendly and pet friendly

Cottage in Vineyard Haven

A living area features a comfortable gray sofa adorned with patterned cushions, positioned beside a light-colored coffee table. A small vase with white flowers sits atop the table, accompanied by two glasses and a bottle. Soft light emanates from a lamp, illuminating the warm wood accents and inviting ambiance.

4.91 out of 5 average rating, 186 reviews

Sweet Cottage w/ yard, 1.5BR, Walk to Town & Water

A charming cottage exterior is showcased, featuring white clapboard siding and black-trimmed windows. A welcoming entrance with double glass doors is flanked by decorative lanterns. Lush greenery and colorful flower beds surround the entrance, creating a vibrant atmosphere.

4.91 out of 5 average rating, 132 reviews

Cozy West End Cottage w/ Parking 1st & 2nd floors

A charming blue cottage is nestled among lush greenery and colorful flowers. The front yard features gravel pathways and two bright blue adirondack chairs, inviting relaxation. Solar panels are positioned on the roof, and a backdrop of trees enhances the tranquil setting.

5 out of 5 average rating, 105 reviews

Quaint Cottage with Backyard Deck, A Perfect Getaway

Cottage in South Yarmouth

A cozy living area features a sectional sofa and a single accent chair in soft blue tones. A glass coffee table sits on a plush area rug, with a gas fireplace integrated into a brick mantel. Natural light enters through large windows, enhancing the warm ambiance.

4.97 out of 5 average rating, 133 reviews

Walk 7/10 mile to Beaches

An open living area is depicted, featuring a comfortable sofa arranged opposite a television on a stand. A breakfast bar with three stools separates the kitchen from the sitting area. Light wood flooring and natural light enhance the inviting ambiance.

4.87 out of 5 average rating, 215 reviews

PET FRIENDLY 1-BR COTTAGE - 3 MIN WALK TO TOWN CTR

A cozy living area is equipped with comfortable seating, including a gray couch and armchair. A nautical-themed rug anchors the space, while a wall clock and decorative items add character. A fireplace against the light-colored wall enhances the welcoming atmosphere, with a view of the kitchen beyond.

4.94 out of 5 average rating, 224 reviews

Walk to beach - firepit - fireplace

Private cottage rentals

4.99 out of 5 average rating, 130 reviews

A circular stone fire pit is surrounded by four white Adirondack chairs, offering a cozy gathering spot. Flames flicker above a bed of decorative stones, casting a warm glow. A smooth patio surface extends around the area, enhancing the outdoor experience.

Cottage in West Dennis

Fall Smores! Close to beach w/modern amenities

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.

4.89 out of 5 average rating, 105 reviews

Oyster Isle-Steps from the Beach!

4.9 out of 5 average rating, 177 reviews

A charming cottage exterior is surrounded by lush greenery and blooming rose bushes, with a white picket fence enclosing the front yard. The gabled roof and shingle siding complement the tranquil landscape, offering a welcoming first impression.

Cottage in New Seabury

Quaint Cape Cod Cottage on a Private Beach!

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!

4.94 out of 5 average rating, 34 reviews

A cozy sleeping area features a spacious bed with plush bedding and decorative pillows. Two bedside tables with lamps are positioned beside the bed. A soft rug with a whale design adorns the bamboo floor, adding comfort to the space.

Cottage in Brewster

Cozy Cottage

4.99 out of 5 average rating, 226 reviews

The cottage is set amidst lush gardens, featuring a wooden archway adorned with hanging planters and red flowers. A stone pathway leads up to the charming entrance, surrounded by vibrant greenery and trees under a clear blue sky.

Cottage in North Eastham

The Salt Pond Cottage

4.92 out of 5 average rating, 162 reviews

Cottage in Hyannis Port

Cape Cottage - Walk to Beach, Ferries, and Town!