Vacation Rentals in Chatham, MA

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Chatham, MA holiday rentals
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1379 Holiday rentals and Airbnb in Chatham, MA

The Best Family-Focused Holiday Rentals in Chatham, MA

Give the kids instant backyard beach fun and plenty of room to unwind at spacious family holiday rentals in Chatham, MA.

Charming Coastal Hideaway With Outdoor Shower - Inviting Summer Oasis - Chatham, MA
No reviews

Charming Coastal Hideaway With Outdoor Shower - Inviting Summer Oasis

house, Chatham
This detached property in Chatham is situated 965 metres from Cockle Cove Beach on Nantucket Sound and 483 metres from the Cape Cod Rail Trail.
This family-friendly holiday home for eight guests features three bedrooms, two bathrooms, air conditioning, WiFi, a screened-in porch, and includes daily free tickets to local attractions through Xplorie, such as whale watching and bike rentals.
Waterfront On Pond W/ Private Beach! - Chatham, MA
No reviews

Waterfront On Pond W/ Private Beach!

house, Chatham
This detached house offers direct waterfront access to Schoolhouse Pond in Chatham, providing a private beach for swimming and fishing, with every room benefiting from serene pond views.
This spacious 2,500 sq ft property accommodates up to nine guests across four bedrooms and three bathrooms, featuring vaulted ceilings, exposed beams, hardwood floors, a wrap-around deck, a detached garage apartment, WiFi, and an enclosed outdoor shower.
Water Views And Kayaking - Charming Cottage Retreat - Chatham, MA
No reviews

Water Views And Kayaking - Charming Cottage Retreat

cottage, Chatham
This recently updated holiday home is situated directly on the sandy beach of Goose Pond in Chatham, offering private freshwater access for swimming, canoeing, and kayaking, and is located 3.2 kilometres from Ridgevale Beach on Nantucket Sound.
This dog-friendly accommodation sleeps four guests in one bedroom with one bathroom, and features a kitchen with a fridge and microwave oven, air conditioning, Wi-Fi, Direct TV, a private outdoor shower, and includes complimentary daily tickets worth $750 through Xplorie for local attractions.
Chatham: Tennis, Water Views/access, Pet Friendly! - Chatham, MA
10 90 reviews

Chatham: Tennis, Water Views/access, Pet Friendly!

apartment, Chatham
This waterfront estate in Chatham is located just 3.2 kilometres from the town's Main Street, offering stunning views of Nantucket Sound and Stage Harbor. The property has received excellent ratings for its location, cleanliness, and overall experience.
This spacious house can comfortably accommodate up to 10 guests and features a well-equipped kitchen, a garden, and a private beach access. Guests can enjoy a variety of on-site amenities, including a tennis court, a bocce court, and a boathouse with a dock, making it ideal for families and groups looking for a relaxing and active getaway.

Holiday Rentals with a Pool in Chatham, MA

Walk right out of your kitchen and jump into a crystal-clear swimming pool at island holiday rentals in Chatham, MA.

The Barn At Chatham Oaks - Chatham, MA
9.6 12 reviews

The Barn At Chatham Oaks

apartment, Chatham
This Chatham holiday home is situated near the sea, less than 2km from the Chatham Chamber of Commerce and Cape Cod beaches, with Ridgevale Beach and Cockle Cove Beach also within 3km.
This 372 square metre property boasts seven bedrooms, five bathrooms, sleeps sixteen guests, and includes a private pool, sauna, and fully equipped kitchen; free Wi-Fi is also provided.
Enjoy Harwich, Pool, Large Hot Tub & Ac! - Chatham, MA
No reviews

Enjoy Harwich, Pool, Large Hot Tub & Ac!

house, Harwich
This Harwich property is located 19 kilometres from Nauset Lighthouse and 21 kilometres from Wellfleet Bay Wildlife Sanctuary, offering convenient access to nearby Cape Cod attractions.
This detached house, covering 191 square meters, accommodates up to 31 guests with its 1 bedroom and 3 bathrooms, featuring a private balcony, hot tub, air conditioning, and complimentary Wi-Fi.
Pool, Half Mile To Beach! - Chatham, MA
No reviews

Pool, Half Mile To Beach!

house, Harwich
This Harwich holiday home is located on a hill, 805 metres from Jackknife Beach and 644 metres from Wequassett Resort, with downtown Chatham a 4.8 kilometre drive away.
This five-bedroom property accommodates up to ten guests and features an outdoor swimming pool, air conditioning, a dishwasher, and indoor entertainment including air hockey and ping pong tables, with pets welcome for a fee.
Hiawatha: 177-cc  Gorgeous Chatham Estate With Heated Pool, Walk To Town Or Beach - Chatham, MA
10 6 reviews

Hiawatha: 177-cc Gorgeous Chatham Estate With Heated Pool, Walk To Town Or Beach

apartment, Chatham
This Chatham holiday home, located 0.5 km from Oyster Pond Beach and 0.6 km from Chatham's High Street, offers easy access to Chase Park, the Godfrey Windmill, and the Chatham Labyrinth.
The 387 square metre property boasts seven bedrooms, six bathrooms, sleeping up to fifteen guests, and features a chef's kitchen, multiple lounges, a heated pool, hot tub, game room, and extensive outdoor spaces.

Frequently asked questions about holiday rentals in Chatham, MA

  • What are some interesting places to visit in or near Chatham, MA?

    Chatham is full of charming spots! You can visit the Chatham Lighthouse, a historic landmark with stunning views, or explore the Chatham Historical Society Museum to learn about the town's rich history. If you're a nature enthusiast, head to the Chatham Bars Inn Beach for a relaxing day by the sea, or take a walk through the scenic Chatham Cranberry Bogs.
  • What are the best Airbnb and holiday rentals in Chatham, MA?

    In-town - Pied-a-terre - Private - Sunny Comfy Home, Chatham Walk To Cape Cod Beach and The Secret Garden are among the best Airbnb and holiday rentals in Chatham, MA.

  • Which walking or cycling routes are the best in Chatham, MA?

    The Chatham Rail Trail is a great choice for both walking and cycling, stretching along the former railroad line. If you're looking for a more scenic route, try the Chatham Coastal Trail, which offers beautiful views of the Atlantic Ocean. For a shorter walk, explore the Chatham Light Beach, a lovely stretch of sand with the iconic lighthouse in the background.
  • What are the most popular Airbnbs in Chatham, MA?

    Among the Airbnbs in Chatham, MA, In-town - Pied-a-terre - Private - Sunny Comfy Home, Chatham Walk To Cape Cod Beach and The Secret Garden are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Chatham, MA?

    Chatham is a haven for outdoor enthusiasts. You can enjoy swimming, sunbathing, and surfing at the many beaches, like Lighthouse Beach and Hardings Beach. For something more adventurous, try kayaking or paddleboarding in the calm waters of Stage Harbor. If you're visiting in the winter, don't miss the chance to go ice skating at the Chatham Municipal Rink.
  • What are the best holiday rentals with a pool in Chatham, MA?

  • What other towns or cities can be easily accessed from Chatham, MA?

    Chatham is conveniently located near other charming towns on Cape Cod. You can easily drive to nearby towns like Harwich Port, Dennis, and Orleans, each offering its unique charm and attractions. For a slightly longer drive, you can visit the bustling town of Hyannis, known for its ferry service to the islands and its vibrant nightlife.
  • What are the best rentals for families and kids in Chatham, MA?

  • What amenities are commonly available in vacation rentals in Chatham, MA?

    Vacation rentals in Chatham typically offer a range of amenities, from fully equipped kitchens and comfortable living spaces to outdoor decks and patios. Many rentals also include amenities like laundry facilities, Wi-Fi, and cable TV. Some rentals even offer extras like private pools, hot tubs, and fireplaces.
  • What are the best rentals or Airbnbs with a jacuzzi in Chatham, MA?

  • What time of year is best to rent a vacation rental Chatham, MA?

    The best time to rent a vacation rental in Chatham depends on your preferences. Summer is the peak season, offering warm weather and plenty of outdoor activities. Spring and autumn provide a more relaxed atmosphere with pleasant temperatures and fewer crowds. If you're looking for a winter escape, Chatham offers a charming and peaceful experience with opportunities for winter sports.

Popular destinations

Holiday Rentals with a Balcony in Chatham, MA

Wake up to the soothing sights and sounds of blue ocean waters directly from your private rental balcony in Chatham, MA.

Waterfront, No Pet Fee, Fenced Yard, Close To Town And Beach - Chatham, MA
10 13 reviews

Waterfront, No Pet Fee, Fenced Yard, Close To Town And Beach

apartment, Chatham
This waterfront apartment is located in Chatham, just a short distance from Cape Cod Beaches and Cape Cod National Seashore, offering a tranquil setting with beautiful views. It has received excellent user ratings, making it a popular choice for travellers.
The apartment spans 195 square metres and can comfortably accommodate up to 10 guests. It features a spacious deck with alfresco dining, a finished basement with ample space for relaxing, and private access to the water, perfect for kayaking, paddleboarding, or simply enjoying the scenery.
Cape Escape Chatham 5 Star Beach Chic 5 Min Walk To Beach-newly Renovated Private Retreat Ac - Chatham, MA
10 1 review

Cape Escape Chatham 5 Star Beach Chic 5 Min Walk To Beach-newly Renovated Private Retreat Ac

house, Chatham
This newly renovated private retreat in Chatham is located 500 metres from the beach and 27 kilometres from Forest Beach, with Nauset Lighthouse 24 kilometres away.
This 158 square metre holiday home sleeps 18 guests across three bedrooms and two bathrooms, offering air conditioning, Wi-Fi, a kitchen, barbecue facilities, and complimentary bicycles.
Chatham Retreat - Chatham, MA
No reviews

Chatham Retreat

house, Chatham
House listing. This accommodation is based in Chatham.
Facilities and services: a kitchen, a dish washer and an iron. This house is very convenient for families.
Walk To Water, Near Downtown Chatham! - Chatham, MA
8.4 6 reviews

Walk To Water, Near Downtown Chatham!

apartment, Chatham
This Chatham holiday home, situated in North Chatham on a private road, is a short walk from Ryder's Cove beach, less than 1.6km from Chatham Perk coffee shop, and just over 3.2km from Chatham's Main Street and the Chatham Lighthouse.
This spacious 164 square metre property offers four bedrooms, two bathrooms, sleeps eight guests, and includes amenities such as Wi-Fi, a fully equipped kitchen, and a private garden with parking; pets are welcome (charges apply).

Best Chatham, MA holiday rentals with parking

80 M² Cottage ∙ 1 Bedroom ∙ 4 Guests - Chatham, MA
9.6 21 reviews

80 M² Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage, Chatham
This Chatham, Massachusetts holiday home is situated on the shores of Goose Pond, 4.2km from Chatham's town centre and its attractions, including the Orpheum Theatre and Chatham Bars Inn, and within 1.6km of local shops and restaurants.
This 80 square metre self-catering property sleeps four guests in one bedroom and one bathroom, boasting a recently updated kitchen and bathroom, a spa, fitness centre, free Xplorie tickets for local attractions, and two kayaks for use on Goose Pond, plus keyless entry and direct beach access.
Two Bedroom Condo Close To Beach - Chatham, MA
9.9 66 reviews

Two Bedroom Condo Close To Beach

apartment, Chatham
This two-story Chatham condo, situated in West Chatham Village, is a 15-minute walk (approx. 2.4km) from Ridgevale Beach, close to Marion's Pie and the Cape Cod Rail Trail.
The property offers two bedrooms, two bathrooms, sleeps five guests, and features two assigned parking spaces, upper and lower decks, an enclosed outdoor shower and grill, plus a fully equipped kitchen including a dishwasher.
Idyllic Cape House Close To Beaches - Chatham, MA
9.9 77 reviews

Idyllic Cape House Close To Beaches

apartment, Chatham
This four-bedroom Chatham house, perfect for families or large groups, is situated within walking distance of Chatham's shops, restaurants, and bars, and close to the town's beaches and ponds.
The 4-bedroom, 2-bathroom property sleeps eight, boasts a finished basement suite with a queen bed and twin sofa bed, a workspace loft, a large garden with a Weber grill, and ample storage for beach equipment.
Central Ac, Game Room, Dog-friendly! - Chatham, MA
10 2 reviews

Central Ac, Game Room, Dog-friendly!

apartment, Chatham
This dog-friendly flat in Chatham is situated less than a 10-minute drive from Hardings Beach, Ridgevale Beach, and Cockle Cove, and a short drive from the Monomoy National Wildlife Refuge and Chatham's Main Street.
This accommodation offers three bedrooms and two bathrooms for up to six guests, featuring a fully equipped kitchen, air conditioning, a garden with a propane grill and firepit, and a game room with a pool table.

Discover Luxury Holiday Rentals in Chatham, MA

Live the ultimate tropical fantasy in properties boasting high-end coastal architecture and absolute privacy at luxury holiday rentals in Chatham, MA.

Delightful Chatham Cottage, Cheerful And Clean - Chatham, MA
9.6 164 reviews

Delightful Chatham Cottage, Cheerful And Clean

apartment, Chatham

Downtown Holiday Rentals in Chatham, MA

Stay steps away from local fish markets, surf shops, and seashore bars at holiday rentals in the heart of Chatham, MA.

Charming 2 Bedroom Condo On Private Beach By Outer Most Marina - Chatham, MA
9.6 8 reviews

Charming 2 Bedroom Condo On Private Beach By Outer Most Marina

apartment, Chatham
"Escape Hatch' Chatham, In Town Location - Chatham, MA
9.9 57 reviews

"Escape Hatch' Chatham, In Town Location

apartment, Chatham
Seaside Condo With Patio, Beach Access, Loft, Board Games, Gas Grill, & Firepit - Chatham, MA
10 1 review

Seaside Condo With Patio, Beach Access, Loft, Board Games, Gas Grill, & Firepit

apartment, Chatham
Chatham Getaway - Chatham, MA
9.9 161 reviews

Chatham Getaway

house, Chatham

Seashore Holiday Rentals in Chatham, MA

Open your glass doors and step directly from your living room onto the warm sand at seashore holiday rentals in Chatham, MA.

Elegant Chatham Home, Steps To Private Association - Chatham, MA
9.7 21 reviews

Elegant Chatham Home, Steps To Private Association

apartment, Chatham
Walk To Ryder Cove Wet Bar & Hot Tub - Chatham, MA
No reviews

Walk To Ryder Cove Wet Bar & Hot Tub

house, Chatham
Slate House - A Modern Waterfront Getaway - Chatham, MA
9.9 320 reviews

Slate House - A Modern Waterfront Getaway

apartment, Chatham
Central Air And Outdoor Living Space - Stunning Coastal Haven - Chatham, MA
10 4 reviews

Central Air And Outdoor Living Space - Stunning Coastal Haven

house, Chatham

Holiday Rentals with a Hot Tub in Chatham, MA

Watch the sun set over the horizon while soaking in a steaming outdoor hot tub at island holiday rentals in Chatham, MA.

Luxury Beach Barn With Pool, Hot Tub & Sauna - Chatham, MA
10 1 review

Luxury Beach Barn With Pool, Hot Tub & Sauna

house, Chatham
229 M² House ∙ 4 Bedrooms ∙ 8 Guests - Chatham, MA
No reviews

229 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Harwich
Charming Harwich Homerelax & Explore Cape Cod - Chatham, MA
No reviews

Charming Harwich Homerelax & Explore Cape Cod

apartment, Harwich
Newly Renovated Guest House For 10 Near The Beach! - Chatham, MA
10 6 reviews

Newly Renovated Guest House For 10 Near The Beach!

apartment, Harwich
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