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!

4.86 out of 5 average rating, 429 reviews

The vintage beach cottage is depicted with a light blue exterior, settled near the edge of a sandy beach. Waves gently crash against the shoreline while a lush green area surrounds the cottage, providing a serene coastal setting. A single vehicle is parked near the entrance.

Cottage in East Sandwich

Bold Oceanfront Cottage w/Pvt Beach ~ Lil Sea Sass

RARE: DIRECT OCEANFRONT & BEACHFRONT CAPE COD COTTAGE — DOG FRIENDLY — LOCATED ON THE COTTAGE’S VERY OWN PRIVATE BEACH! Lil’ Sea Sass is a 3 BR vintage beach cottage that is nestled in the dunes offering unparalleled ocean views and is located in a very private serene setting. This oasis is near the end of a private road and then down a long drive — with free guaranteed parking for 2+ cars! Amenities include: gas fireplace, fire table, FAST WIFI, central AC & heat, and an outdoor shower.

4.96 out of 5 average rating, 139 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*

Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & sofa set in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps & DirectTV 🛋️ Comfy Furnishings➕Stocked Kitchen Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

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.

4.97 out of 5 average rating, 275 reviews

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, 390 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.

4.97 out of 5 average rating, 347 reviews

A cozy outdoor seating area is arranged with several white lounge chairs on a gravel surface. A brick fireplace is positioned near the house, accompanied by potted plants and a view of the deck area adorned with covered furniture in the background.

Cottage in West Chop

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

Cottage in South Yarmouth

A bright living area is presented with a deep blue sectional sofa, facing a mounted Roku TV above a white fireplace. A wooden coffee table is centered in front of the sofa, with a dining table visible in the background, complemented by stylish light fixtures and chic wallpaper.

4.99 out of 5 average rating, 189 reviews

LUXHOME★Walk2Beach★Firepit★PetOK★Kingbed

⚓️ THE SALT HOUSE⚓️ 👍🏼WFH desk/1200 Mbps wifi speed 👍🏼fenced in yard 👍🏼pet friendly ($30/per night pet fee) 👍🏼luxury bedding 👍🏼Roku tv in every room 👍🏼outdoor shower 👍🏼propane fire pit 👍🏼beach bikes 🏖1/2 mile walk to Parker’s River Ocean Beach, 🦞Skippers Restaurant/ice cream (Appx 10 min walk/5min bike ride! Under 5 min drive to -The Cape Cod Inflatable Water Park -The Whydah Pirates Museum -Pirates Cove Mini Golf -Skull Island Arcade with Go-Karts/batting cages

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.

4.93 out of 5 average rating, 188 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.

4.99 out of 5 average rating, 171 reviews

The cottage exterior features a charming white facade with several windows illuminated in warm light. A welcoming front porch is adorned with potted plants, and an American flag is displayed. The surrounding lawn is well-maintained, enhancing the inviting atmosphere.

Cottage in Barnstable

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

4.86 out of 5 average rating, 563 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

Cottage in South Yarmouth

A light-filled living area features a navy blue sofa and striped accent chairs, complemented by a natural fiber rug. A flat-screen TV is mounted above a white fireplace, with wall art displayed on the blue walls. Windows allow natural light to enhance the space.

4.9 out of 5 average rating, 134 reviews

Memorable Moments Cottage

Amazing Beach House for Family & Friends. 4 miles to the closest Beach. Beach parking pass available for Barnstable. (9+ beaches and ponds in the Yarmouth area, this parking is not included in the beach pass) Minutes away to great Restaurants, Museums, Mini golf, Ice Cream and so much more. The newly renovated cottage has hardwood floors, updated fully equipped kitchen, Streaming TV, WiFi, high speed internet, and washer and dryer.

4.95 out of 5 average rating, 200 reviews

A bright living area features wooden beams across the ceiling and light walls. A comfortable couch with decorative pillows faces a coffee table stacked with magazines. Two lamps provide ambient lighting, while sunlight enters through multiple windows, creating a welcoming environment.

Cottage in East Falmouth

“Cozy Cottage” on Great Bay

Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach. We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

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, 291 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

5 out of 5 average rating, 10 reviews

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.

Cottage in Dennis Port

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.

Cottage in Dennis Port

4.79 out of 5 average rating, 87 reviews

Best Little Beach Cottage!

4.93 out of 5 average rating, 28 reviews

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.

Cottage in Provincetown

NEW! East End Cottage with Private Hot Tub!

Superhost

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.

Private room in Onset

4.7 out of 5 average rating, 44 reviews

The Crab Cottage@The Compound Beach Resort Habitat

4.88 out of 5 average rating, 34 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

Superhost

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

4.87 out of 5 average rating, 38 reviews

The Front Cottage: Waterfront/Dock/Hot tub

Pet-friendly cottage rentals

4.81 out of 5 average rating, 502 reviews

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.

Cottage in Provincetown

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

4.94 out of 5 average rating, 154 reviews

A sandy beach area is visible, with gentle waves lapping at the shore. A wooden pathway leads down to the water, surrounded by sparse trees and shrubs. The scene is framed by a clear blue sky and distant greenery, creating a serene coastal view.

Cottage in Oak Bluffs

Charming water-front cottage on Martha's Vineyard!

4.98 out of 5 average rating, 211 reviews

A bright bedroom features a spacious bed with colorful blankets and decorative pillows. A variety of sun hats are displayed on the wall, providing a cheerful accent. Natural light enters through the window, illuminating the cozy interior.

Cottage in Dennis

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

4.96 out of 5 average rating, 192 reviews

The kitchen features modern stainless steel appliances, including a refrigerator and microwave. A spacious island with seating for three is highlighted by pendant lighting. Light streams in through the windows, complementing the sleek cabinetry and clean countertops.

Cottage in Oak Bluffs

Beautiful walk to Town, Inkwell and harbor!

4.79 out of 5 average rating, 118 reviews

The charming beach cottage features a light-colored exterior with multiple windows, framed by lush greenery and well-maintained bushes. A grassy lawn leads to the entrance, with a clear path visible and surrounding trees providing a natural backdrop.

Cottage in Bourne

Adorable Gray Gables Beach Cottage

5 out of 5 average rating, 106 reviews

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.

Cottage in Provincetown

Quaint Cottage with Backyard Deck, A Perfect Getaway

4.96 out of 5 average rating, 152 reviews

Soft waves gently lap against smooth stones along a sandy beach. The tranquil water reflects the pastel hues of the sky, creating a serene coastal scene. In the distance, small waves ripple towards the horizon.

Cottage in Plymouth

Coastal Cottage — 7 min walk to private beach

Private cottage rentals

A cozy lounge area features two light-colored sofas adorned with decorative pillows, positioned around a textured area rug. A wooden ladder leads to a lofted space, while natural light is welcomed through a skylight above. The stone fireplace adds warmth to the inviting atmosphere.

4.94 out of 5 average rating, 49 reviews

Chatham Beach Cottage 2BR + Loft Walk to the Beach

Superhost

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

4.9 out of 5 average rating, 239 reviews

Classic Cape Cod Cottage

Cottage in Harwich Center

A serene beach setting is captured, featuring soft, sandy shores leading to calm waters. A few buoy markers float on the water's surface. In the distance, trees and homes line the shoreline beneath a partly cloudy sky.

5 out of 5 average rating, 72 reviews

Bucks Pond Cottage w/Central A/C & Linens

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.

4.95 out of 5 average rating, 76 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

4.98 out of 5 average rating, 56 reviews

The cottage exterior features a grey shingled facade and a welcoming front porch with multiple windows. A gravel driveway leads to the entrance, flanked by neatly landscaped grass and shrubs. An American flag decorates the entrance, enhancing the charming curb appeal.

Cottage in Harwich Port

Harwich Port Cottage, Close to Town & Beaches

The main living area features blue walls adorned with coastal art, creating a serene ambiance. A comfortable navy couch is placed near a white side table, with a round mirror reflecting light. The ceiling beams add architectural interest, while natural light flows through the skylight.

4.99 out of 5 average rating, 79 reviews

Walk to Beach - Family Friendly - Fireplace

5 out of 5 average rating, 25 reviews

A bright and airy bedroom is presented with a spacious bed, complemented by soft bed linens and decorative pillows. Two armchairs are placed in front of the bed, with a wooden side table between them. Natural light enters through windows adorned with light curtains.

Cottage in Hyannis

Cozy Cottage w/Fireplace•Firepit•by Shops+Dining