Chatham vacation rentals

4.92 out of 5 average rating, 109 reviews

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

4.87 out of 5 average rating, 152 reviews

The serene water reflects the soft colors of a sunset, with hints of pink and orange blending into the sky. Lush greenery surrounds the calm water, creating a tranquil atmosphere. Gentle ripples are visible on the surface, enhancing the peaceful setting.

Home in Hyannis Port

Cottage with private beach in Hyannis Port

Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!

5 out of 5 average rating, 5 reviews

An open-concept living area showcases a blend of wood and tile flooring, enhancing the spacious feel. The kitchen features wooden cabinetry and black granite countertops, with seating available nearby. Natural light pours in through large windows, illuminating the modern decor in the inviting living space.

Condo in Provincetown

Spacious Ptown Escape | Patio, AC, 2-Car Parking

We've been renting this for years, and our previous listing had 125 reviews and a 4.98 star rating! Experience modern coastal charm at our stylishly designed 2-bedroom vacation rental, ideally situated just a short stroll from the stunning beaches and vibrant attractions of Provincetown. With thoughtful decor, a prime location, parking for 2 vehicles, and a welcoming atmosphere, this getaway is the perfect way to experience Provincetown like a local and for creating unforgettable memories.

4.88 out of 5 average rating, 153 reviews

An open kitchen and dining area features a rustic wooden farm table set for six, surrounded by natural light from large windows. A well-equipped kitchen with a stainless steel stove and a wooden bar area with stools is visible, complemented by warm wood tones throughout.

Home in Yarmouth Port

* Walk to the beach - Swiss Beach House! *

Walk to the beach! Less than a 1/2 mile (0.7 km)! Perfect spot for paddle boarding. Paddleboards and gas grill (available in summer). Private European - style house. Rustic charm. Laid-back atmosphere. 3 Bedroom, 2.5 bathroom. Comfortably sleeps 6-7, up to 8. Fire pit. Outdoor shower. Farm table for group dining. Fantastic central Cape Cod location. Natural environment. 15 min. to Hyannis for ferries to Nantucket or Martha's Vineyard. Enjoy something unique. Experience the real Cape Cod.

4.95 out of 5 average rating, 168 reviews

The kitchen features a spacious granite countertop with seating at three bar stools. Large windows and overhead lighting enhance the bright and airy atmosphere. Appliances including a stove and refrigerator are integrated into the cabinetry, providing a modern look in the renovated space.

Apartment in Oak Bluffs

Beautiful private apartment walk to everything!

This is an incredible property! Renovated and spotless with all the amenities to make your stay feel like home, only better. Downtown Oak Bluffs and her beautiful beaches are within a five-minute walk. There is a local market and deli right next door where you can find anything you need in a pinch, and a great BBQ restaurant across the street. This second floor apartment has one bedroom with a queen-sized bed and a queen pullout couch. Smart TVs, full kitchen and laundry plus much more!

5 out of 5 average rating, 29 reviews

A serene outdoor area features four black Adirondack chairs arranged around a small fire pit on lush green grass. The cottage's charming exterior, highlighted by a wooden deck and American flag, is visible in the background, surrounded by trees.

Home in Sandwich

The Cape Cottage Fireplace * Kid Friendly * PetsOK

The Cape Cottage is a private, tranquil Cape Cod-style cottage nestled near historic downtown Sandwich and just 6 minutes from the ocean. Newly renovated, this home is tastefully designed with a blend of coastal, farmhouse and antique design elements. We thoughtfully curated the home's details to evoke the comforts of home and give it unique charm that pays homage to quintessential New England and Cape Cod's scenic beauty. Check out our IG @thecapecodcottage for more pictures and vibes.

4.85 out of 5 average rating, 62 reviews

A tranquil outdoor space features white lounge chairs positioned on a grassy area, overlooking Cape Cod Bay. Vibrant flowers in the foreground add color, while serene water views and tree foliage create a peaceful natural setting.

Cottage in Brewster

BeachFront Private Beach Amazing Views WIFI

Sunset Cottage, Amazing Location on a secluded bluff, with fantastic views of Cape Cod bay, Beach front! A/C WIFI Simple Cottage, natural setting, safe quiet clean Beautiful huge Private beach for 3 cottages and the main house. All photos are on the property Desirable Brewster MA on the Bay. Amazing sunset views over the ocean from every room. Full kitchen, large living room, Master Queen bedroom, 2nd queen bedroom (coolgel matress), Long wide private beach. 360 feet long!!

4.81 out of 5 average rating, 474 reviews

A covered porch area features wicker seating with decorative cushions, inviting relaxation. A small table is positioned between the chairs, with a view of a landscaped yard visible through the railing. Potted flowers add a splash of color, enhancing the outdoor ambiance.

Cottage in Provincetown

Private cottage green friendly and pet friendly

. Private quiet Restored and renovated stand alone cottage in the west end location complete with new renovation of kitchen and bathroom. Recently added an Extended bay window, new skylight, and brand new dishwasher Green friendly and pet friendly From June 28 to September 10 this is only a Saturday to Saturday rental only . Bear week and carnival week is a surcharge of $50 more per night. When you bring a pet there is a separate cleaning fee of $40 non refundable

4.93 out of 5 average rating, 41 reviews

An aerial view of the lake house is presented, showcasing its two-story structure and surrounding wooden fence. The property is adjacent to the serene lake, with a clear view of the water and nearby trees, enhancing the natural setting.

Home in Plymouth

The Lake House Paradise!

Escape to our serene lake house with breathtaking views & endless opportunities for outdoor adventure. With a dedicated workspace, stay connected while enjoying tranquility. Take a paddle on the lake with kayaks & pedal boat, or relax on the patio with outdoor fire pit. Fully furnished & decorated, feel at home cooking in the fully equipped kitchen or curling up in the cozy living room. Book your stay today and experience the magic of nature firsthand!

Guesthouse in Provincetown

An open studio cottage features a colorful orange refrigerator against a backdrop of botanical wallpaper. A cozy couch is positioned beside a kitchenette that includes a farmhouse sink. Light wood beams and tile flooring add charm to the inviting living space.

5 out of 5 average rating, 68 reviews

Central Cottage-Incredible Location, Stylish Charm

Beautifully renovated cottage in incredibly central Provincetown location! Less than a block to The Boatslip and the beach! Open studio cottage has stunning tile throughout, kitchenette, excellent air conditioning, ceiling fan, living area with couch, breakfast bar/desk, farmhouse sink, 1 queen bed, outdoor seating area, shared backyard (with seating, grill, and outdoor shower), and reliable high-speed wifi. Fresh, whimsical styling & worldly charm.

4.91 out of 5 average rating, 54 reviews

Home in Edgartown

Updated Beautiful Cottage in Edgartown AC

A true island charmer. Light, airy and central-air-conditioned home offers all the comforts of modern living centrally located in Edgartown. Recently completed extensive upgrades completed enhance all of the space, including a new kitchen, both bathrooms, basement, and more. A spacious outdoor furnished deck with enclosed outdoor shower and an expansive grassy lawn make for a great space to relax. Great location makes Island travel a breeze.

4.89 out of 5 average rating, 57 reviews

A serene view of a calm water surface reflects a vibrant sunset, blending shades of orange, pink, and purple in the sky. A simple structure is positioned near the shoreline, with silhouetted trees framing the scene, enhancing the natural beauty.

Home in Orleans

Romantic Orleans waterfront cottage

ENHANCED CLEANING/DISINFECTING and SELF CHECK-IN ! The best of Cape Cod - literally on the edge of the gorgeous and picturesque saltwater town cove! This beautiful 1BR cottage is clean, comfortable and private, ... yet within a short walk to village center, shops, great eateries, attractions, etc. We just added propane fire pits and bluetooth speakers outside!!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Chatham vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Chatham's top sights

Chatham Squire44 locals recommend

Chatham Bars Inn49 locals recommend

Chatham Pier Fish Market34 locals recommend

Lighthouse Beach35 locals recommend

Impudent Oyster25 locals recommend

Bluefins Sushi & Sake Bar29 locals recommend

Other great vacation rentals in Chatham

4.99 out of 5 average rating, 143 reviews

A circular arrangement of chairs in various colors surrounds a small stone fire pit. The scene overlooks a serene pond, framed by lush trees and bathed in warm sunlight. Subtle outdoor lighting is positioned along the perimeter.

Cottage in Hyannis

Beach Glass Cottage - Pond Front

4.7 out of 5 average rating, 56 reviews

The image depicts a sandy beach with gentle waves lapping against a rocky shore. Smooth rocks are partially covered in green moss, and the expansive ocean stretches out under a clear blue sky. The sunlight glimmers on the water's surface.

Cottage in Dennis Port

Great Cottage - Walk to the Beach! (97)

4.91 out of 5 average rating, 67 reviews

A well-lit entryway leads to a carpeted staircase, with wooden handrails and light-colored walls. The open kitchen area is visible in the background, complemented by a dining space to the right, enhancing the spacious feel of the home.

Apartment in Marshfield

FULLY RENO'D apt w/water views near beach& marina

4.95 out of 5 average rating, 19 reviews

A patio area features several white Adirondack chairs arranged around a small table, inviting relaxation. A pergola is visible, with a dining table set for outdoor meals. The pond is seen in the background, framed by trees and a clear sky.

Home in New Seabury

25 Menemsha Rd., Popponesset, pond & beach views

4.93 out of 5 average rating, 14 reviews

Three turquoise Adirondack chairs are positioned on a grassy area, offering a view of a natural pathway lined with trees. The scene is brightened by natural light filtering through the leaves, creating a serene outdoor environment.

Home in Wareham

Private home, secluded 6 acre lot with water view

4.92 out of 5 average rating, 13 reviews

An outdoor seating area features a round table surrounded by several cushioned chairs on a blue area rug. Green decorative pillows add a pop of color, while trees provide a natural backdrop in a peaceful setting. The railings enhance the open, inviting space.

Home in East Falmouth

Jaws House - Great Harbors

4.8 out of 5 average rating, 25 reviews

A comfortable living area is highlighted by large windows allowing natural light to fill the space. Two patterned armchairs and a cozy sofa surround a central coffee table. Decorative items, including wooden wall accents, contribute to the inviting ambiance.

Home in Teaticket

5 Bedroom, Central Air, Close to Beaches and MORE!