Vacation Rentals in Chatham, MA

1379 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Chatham, MA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.

195 M² House ∙ 5 Bedrooms ∙ 10 Guests - Chatham, MA
9.3 6 reviews

195 M² House ∙ 5 Bedrooms ∙ 10 Guests

house, Chatham
This five-bedroom Chatham holiday home is situated in a quiet residential area, less than half a kilometre from Schoolhouse Pond and approximately 0.8 kilometres from the Cape Cod Rail Trail.
The 195 square metre property boasts a spacious layout, sleeping up to ten guests, and includes a game room, private deck with gas grill, a spa, fitness centre and $750 worth of Xplorie tickets to local attractions.
Chatham Home: Backyard, Multi-level Deck, Dogs Ok - Chatham, MA
9.6 100 reviews

Chatham Home: Backyard, Multi-level Deck, Dogs Ok

apartment, Chatham
This dog-friendly two-bedroom holiday flat in Chatham is situated 250 metres from the Barn Hill boat launch and approximately 1.6 kilometres from Hardings Beach, with the town centre just over 3.2 kilometres east.
This well-appointed property accommodates up to six guests and features a gas fireplace, flatscreen television, a sunroom, a well-equipped kitchen, and a multi-level deck, alongside a landscaped garden with beach essentials provided.
Chatham Break! 3 Br, A/c, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard - Chatham, MA
10 108 reviews

Chatham Break! 3 Br, A/c, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

apartment, Chatham
This charming Cape Cod-style house is located in a peaceful Chatham neighbourhood, just a short walk from Oyster Pond and a short drive to downtown Chatham and Hardings Beach. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The property features three bedrooms and one bathroom, accommodating up to six guests comfortably within its 93 square metres of floor space. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private garden, a terrace, a Jacuzzi, and a spa, ensuring a relaxing and enjoyable stay.
Perfect For Group W/ Kids & Dogs W/ Hot Tub - Chatham, MA
No reviews

Perfect For Group W/ Kids & Dogs W/ Hot Tub

house, Chatham
This recently renovated detached house is situated in Chatham's Forest Beach district, under 800 meters from Forest Beach and a short drive from the amenities of Harwich Port and Downtown Chatham.
This dog-friendly property accommodates up to 10 guests across 4 bedrooms, including a unique bunk room, and features a hot tub on the back deck, a spacious semi-fenced private garden with a gas grill, and outdoor shower, alongside WiFi and air conditioning.

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.

Pool And Large Yard! - Chatham, MA
8.4 6 reviews

Pool And Large Yard!

apartment, Chatham
This dog-friendly four-bedroom holiday home in North Chatham offers a private in-ground swimming pool and is conveniently located near Cape Cod Beaches and Cape Cod National Seashore, with the Chatham Railroad Museum and Chatham Marconi Maritime Centre also within easy reach.
This spacious accommodation comfortably sleeps nine guests and features central air conditioning, six televisions, Wi-Fi, a well-equipped kitchen with a microwave and dishwasher, and outdoor amenities including a gas barbecue and an outdoor shower.
Walk 2beach, Pool, Hot Tub, Gameroom, Petsok - Chatham, MA
10 15 reviews

Walk 2beach, Pool, Hot Tub, Gameroom, Petsok

apartment, Chatham
This four-bedroom apartment in Chatham is situated just a short walk from Hardings Beach, offering easy access to the beautiful coastline.
The 334.45 square metre property boasts a private pool and hot tub, a game room, a movie room, and an outdoor kitchen with a fire pit area, providing ample space and entertainment options for up to 10 guests.
Pool, Half Mile To Beach! - Chatham, MA
10 2 reviews

Pool, Half Mile To Beach!

apartment, Harwich
This Harwich holiday home enjoys a hilltop position, less than 1km from Jackknife Beach and 0.6km from the Wequassett Resort.
This five-bedroom property, boasting 236 square metres of floor space, offers four bathrooms, a private pool (seasonal), and accommodates up to ten guests, with added amenities including a games room and parking.
Stones Throw: 052-cs  Alluring Chatham In-town Home With Pool, Walk To It All - Chatham, MA
10 5 reviews

Stones Throw: 052-cs Alluring Chatham In-town Home With Pool, Walk To It All

apartment, Chatham
This in-town Chatham residence is situated 0.4 kilometres from Oyster Pond Beach and a 5-minute walk from Main Street's shops and restaurants.
This 260 square metre apartment offers accommodation for 10 guests, featuring four bedrooms, three bathrooms, a well-equipped kitchen with a dishwasher, air conditioning, a swimming pool, hot tub, and a game room with foosball and air hockey.

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.

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
This Chatham flat provides direct access to Lighthouse Beach and is a short walk from Chatham Harbour and Chatham Lighthouse, offering a historical perspective.
This 52 square meter apartment accommodates up to four guests, featuring one bedroom, a full kitchen, air conditioning, a loft accessible by ladder, an outdoor shower, and a patio area, with board games and books provided.
Spacious W/ Large Outdoor Area Fire Pit! - Chatham, MA
9.4 109 reviews

Spacious W/ Large Outdoor Area Fire Pit!

apartment, Chatham
This seaside property is situated near Chatham, less than 1.6km from the Chatham Shark Center and Veterans Field, and within 3.2km of Gallery Antonia and Mayo House.
This 186 square metre house, sleeping eight guests, boasts four bedrooms, two bathrooms, a fully equipped kitchen, garden, terrace, parking, and in-house laundry facilities; enjoy ocean views and easy beach access.
Luxury Waterfront With Game Room! - Chatham, MA
8.8 3 reviews

Luxury Waterfront With Game Room!

apartment, Chatham
This five-bedroom Chatham holiday home, situated on Crows Pond and Ryder Cove, enjoys waterfront access and is approximately 1.6km from Jackknife Beach.
The 304 square metre property offers a spacious layout sleeping up to 12 guests, boasting a game room with a full bar, updated kitchen, private patio, outdoor shower, and parking for three cars.
Charming Dog Friendly North Chatham Ranch - Chatham, MA
10 2 reviews

Charming Dog Friendly North Chatham Ranch

apartment, Chatham
This pet-friendly holiday flat in North Chatham offers a seaside location, a 13-minute walk to Cape Cod Beaches and a 10-minute walk to the Chatham Shark Centre.
This 132 square metre apartment accommodates up to four guests, featuring two bedrooms, two bathrooms, a kitchen with a fridge, microwave oven and dishwasher, air conditioning, a terrace/balcony, garden, and on-site covered parking.

Best Chatham, MA holiday rentals with parking

Private Beach In Chatham - Sleeps 5 - Chatham, MA
9.8 141 reviews

Private Beach In Chatham - Sleeps 5

apartment, Chatham
This Chatham beachfront apartment offers direct access to a private beach, is less than 1.6km from Chatham town centre with its shops and restaurants, and a short walk from Chatham Lighthouse Beach and the Monomoy National Wildlife Refuge.
Sleeping five comfortably, this two-bedroom, one-bathroom property features a king-size bed, full-size bed, and twin bed, a fully equipped kitchen, keyless entry, Wi-Fi, two parking spaces, and access to an outdoor dining area with a Weber gas grill and an enclosed outdoor shower, plus a fitness centre.
145 M² House ∙ 4 Bedrooms ∙ 10 Guests - Chatham, MA
10 3 reviews

145 M² House ∙ 4 Bedrooms ∙ 10 Guests

house, Chatham
Poppy's Place, situated in a quiet Chatham neighbourhood, is 0.4km from Goose Pond and 1km from Schoolhouse Pond, offering easy access to Chatham's town centre (4.2km) and several beaches.
This four-bedroom, three-bathroom property boasts 145 square metres of space across three levels, sleeping up to ten guests and including a spacious kitchen, a lower-level bonus room, and Xplorie access to local attractions; enjoy a welcome bag and keyless entry.
Private Beach On Pond, Linens Included, Kayak & Canoe. All Rooms W/ Pond Views! - Chatham, MA
10 33 reviews

Private Beach On Pond, Linens Included, Kayak & Canoe. All Rooms W/ Pond Views!

apartment, Chatham
This four-bedroom house is located in South Chatham, just 3.2 kilometres from the charming town centre and within 3.2 kilometres of several beaches. The property has received excellent guest reviews for its comfortable stay and exceptional amenities.
This spacious property can comfortably accommodate eight guests and offers a fully equipped kitchen, three bathrooms, and a private garden. Guests can enjoy a variety of amenities such as a private beach, a peaceful pond with a kayak, canoe, and paddleboard, and a fire pit, making it a perfect choice for families and groups looking for a relaxing getaway.
Pond Front Home W/ Game Room Dog Friendly! - Chatham, MA
9.4 88 reviews

Pond Front Home W/ Game Room Dog Friendly!

apartment, Chatham
This charming house is located just 0.5km from Adventure Chatham and within 5km of the Chatham Chamber of Commerce and Cape Cod Beaches, offering easy access to the area's attractions. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The house spans 223 square metres and comfortably accommodates up to 10 guests. It includes a fully equipped kitchen, a private garden, a gas grill, and a TV for entertainment, making it a perfect choice for families or groups seeking a relaxing and comfortable stay.

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.

Perfect For Group W/ Kids & Dogs W/ Hot Tub - Chatham, MA
9.7 132 reviews

Perfect For Group W/ Kids & Dogs W/ Hot Tub

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.

Private Basement One Bedroom In Owner Occupied - Chatham, MA
9.9 20 reviews

Private Basement One Bedroom In Owner Occupied

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

Chatham Getaway

house, Chatham
Chatham Village - Adorable Studio Apartment In Antique Home - Chatham, MA
9.4 99 reviews

Chatham Village - Adorable Studio Apartment In Antique Home

studio, Chatham
Beautiful Downtown Chatham 1 Bed, Near Oyster Pond - Chatham, MA
10 77 reviews

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

apartment, 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.

Riviera Sunset - Chatham, MA
No reviews

Riviera Sunset

house, Chatham
Hot Tub, Fenced Yard & Dog Friendly - Chatham, MA
9.9 84 reviews

Hot Tub, Fenced Yard & Dog Friendly

apartment, Chatham
Hot Tub, Fenced Yard & Dog Friendly - Chatham, MA
9.8 32 reviews

Hot Tub, Fenced Yard & Dog Friendly

house, Chatham
Slow M'ocean – A Fresh Take On Cape Calm - Chatham, MA
No reviews

Slow M'ocean – A Fresh Take On Cape Calm

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.

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

Walk To Ryder Cove Wet Bar & Hot Tub

house, Chatham
Sail Loft: 489-c  Updated Chatham Family Compound, Heated Pool W/hot Tub, Walk To Town/beach - Chatham, MA
10 21 reviews

Sail Loft: 489-c Updated Chatham Family Compound, Heated Pool W/hot Tub, Walk To Town/beach

apartment, Chatham
Enjoy Harwich, Pool, Large Hot Tub & Ac! - Chatham, MA
No reviews

Enjoy Harwich, Pool, Large Hot Tub & Ac!

house, Harwich
Luxury Home With Pool, Hot Tub & Water View - Chatham, MA
10 2 reviews

Luxury Home With Pool, Hot Tub & Water View

house, Chatham
©2026 cozycozy.com