Cottage vacation rentals in Chatham

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!

4.85 out of 5 average rating, 118 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 Cape Cod winter retreat- 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.

4.96 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 cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. The light wood floor complements the bright blue walls, while a flat-screen TV and a coffee table with remote sit within the space. Natural light filters through large glass doors, overlooking a private patio.

4.92 out of 5 average rating, 507 reviews

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

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, 391 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.

4.96 out of 5 average rating, 251 reviews

Cottage in West Yarmouth

Cozy Coastal Cottage With Sprawling Sea Views

Take in endless views of the ocean walking up to this quaint cottage. Here, the pace is leisurely – sip coffee on the deck, watch the sunrise, and swim in the warm waters of Nantucket Sound just outside. We make changes yearly! A new marble bath was just installed! Close by is downtown Hyannis to shop and eat, mini golf, a water park, ferries to the islands, harbor tours, biking, and more. You will be at peace and filled with serenity staying here on Cape Cod. Can't wait to host you!

4.98 out of 5 average rating, 317 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.

4.97 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.

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.

4.86 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

4.99 out of 5 average rating, 229 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

This is a free-standing private cottage that sleeps 2 comfortably. A spiral staircase leads up to a sleeping loft with a NEW QUEEN size Nectar bed! There is a full futon couch on the main level. The kitchen has everything you may need. The most spectacular thing about this home is its close proximity to the National Seashore. The salt pond, bike path, and freshwater ponds are also moments away!

Popular amenities for Chatham cottage rentals

Kitchen

Wifi

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

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!

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

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

4.93 out of 5 average rating, 125 reviews

The exterior of the cottage features a raised deck with a lattice design, offering a clear view of the entrance. Brightly colored umbrellas and planters add subtle touches to the space. A gravel pathway leads to the stairs, surrounded by greenery.

Cottage in Buzzards Bay

Buzzards Bay - Beach Bungalow

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

An outdoor dining area is presented, featuring a rectangular wooden table surrounded by six rattan chairs. A large striped umbrella provides shade. In the background, a mural of an octopus and the words 'Cape Cod' adorns the cottage wall, enhancing the vibrant atmosphere.

4.97 out of 5 average rating, 115 reviews

Charming Cape Cod Getaway near Beaches

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

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, 228 reviews

Walk to beach - firepit - fireplace

An inviting seating area features two patterned armchairs and a comfortable couch. A round coffee table sits in the center, adorned with candles. Natural light filters through windows with white shades, illuminating the room's warm wood flooring and light green walls.

4.96 out of 5 average rating, 130 reviews

*Tiny Cottage* Dog Friendly*1/2 mile2beach

Private cottage rentals

4.95 out of 5 average rating, 125 reviews

A charming cottage features a red front door and a brick chimney. A patio set with an umbrella is positioned outside, surrounded by a lush green lawn and trees. The exterior showcases a mix of horizontal siding and brick accents.

Cottage in Plymouth

Cozy Ladybug Cottage Near Cape Cod Canal

4.99 out of 5 average rating, 131 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

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.

4.94 out of 5 average rating, 48 reviews

"Escape Hatch' Chatham, In town Location

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!

4.89 out of 5 average rating, 299 reviews

A wooden boardwalk stretches through a lush green landscape, featuring tall trees on either side. The path is lined with wooden railings, creating a serene and inviting atmosphere that leads deeper into the natural surroundings.

Cottage in Wellfleet

The Perfect Getaway in Wellfleet

A charming Cape cottage is framed by lush greenery, with sections of neatly mulched garden beds featuring flowering plants. An American flag hangs at the entrance, complemented by a stone walkway leading to the front door. The property is bathed in natural sunlight.

4.92 out of 5 average rating, 133 reviews

Cape Escape-The Perfect Getaway

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.