Holiday Rentals in Chatham, MA

1015 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Chatham, MA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Chatham, MA

Best family friendly Chatham, MA holiday rentals

Among the 1015 accommodations in Chatham, MA, here are the 4 best family friendly rentals

Captain Alexanders Spa & Putting Green Not A Vacation Home But A Destination. - Chatham, MA
9.3 84 reviews
Chatham, MA
04/08 – 08/08
£435/nighttotal: £1740 (4 )

Captain Alexanders Spa & Putting Green Not A Vacation Home But A Destination.

2 2
apartment , Harwich
This Harwich property is just a short walk from Cape Cod Beaches and Earle Road Beach, offering a peaceful escape from the hustle and bustle of town. The house has received excellent guest ratings, making it a popular choice for travellers.
This three-bedroom holiday home provides ample space for families or groups. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, a swimming pool, a Jacuzzi and a spa, as well as free Wi-Fi access.
Posh Pad With King Beds Central A/c - Chatham, MA
8.6 4 reviews
Chatham, MA
15/08 – 22/08
£840/nighttotal: £5880 (7 )

Posh Pad With King Beds Central A/c

4 10
cottage , Harwich
This 4-bedroom Cape Cod holiday home is located on a quiet, tree-lined street in Harwich, a short drive from Cape Cod Beaches and Mayflower Beach, and convenient to Adventure Chatham and Cape Cod Lavender Farm.
This 130 square meter property accommodates up to 12 guests and features central air conditioning, a fully equipped kitchen, a fireplace, an outdoor shower, and is ideal for water activities and hiking.
Captain's Quarters @ Captain Alexander's Hideaway 5 Minute Walk To The Beach - Chatham, MA
8.6 7 reviews
Chatham, MA
04/08 – 08/08
£313/nighttotal: £1252 (4 )

Captain's Quarters @ Captain Alexander's Hideaway 5 Minute Walk To The Beach

1 2
apartment , Harwich
This cosy apartment is located in West Harwich, just a short walk from Earle Road Beach and a mile from the charming village of Harwichport. It has been consistently rated very good by previous guests.
The apartment is compact, measuring just 14 square metres, but is equipped with everything you need for a comfortable stay. You can enjoy the private yard with an outdoor shower, a gas grill, and a table and chairs, and stay connected with high-speed internet.
5br 3.5 Ba, 2 Wing Home, Ac, Foosball, Fenced Yard, Beach ~1 Mi - Chatham, MA
9.8 40 reviews
Chatham, MA
15/08 – 22/08
£604/nighttotal: £4228 (7 )

5br 3.5 Ba, 2 Wing Home, Ac, Foosball, Fenced Yard, Beach ~1 Mi

5 10
apartment , Harwich
This five-bedroom property is located on the beach side of Route 28 in South Harwich, just over a mile from Red River Beach and a short distance from Chatham. The house has received excellent user ratings, reflecting its high standard of comfort and convenience.
The spacious house, spanning 251 square metres, comfortably accommodates up to 10 guests. Amenities include a fully equipped kitchen, a basement game room, a fenced backyard with a patio and fire pit, and central air conditioning.

Compare Self-Catering Holiday Rentals with a Swimming Pool in Chatham, MA

A holiday rental or Airbnb with a swimming pool near the water in Chatham, MA is a brilliant base for a relaxing swim. View our collection.

Breathtaking Harwich Retreat W/ Heated Pool And Spa Rpam086 - Chatham, MA
10 4 reviews
Chatham, MA
15/08 – 22/08
£1945/nighttotal: £13615 (7 )

Breathtaking Harwich Retreat W/ Heated Pool And Spa Rpam086

4 10
apartment , Harwich
This Harwich holiday home, near Red River Beach (1.9 km) and Bank Street Beach (3 km), offers easy access to Harwich Port (2.9 km) and Chatham (7.7 km).
The 339-square-metre property boasts four bedrooms, four bathrooms, sleeps up to sixteen guests, and includes a 20x40ft heated swimming pool, hot tub, and fully equipped gourmet kitchen.
Heated Pool Ac 1/2 Mile To Beach! - Chatham, MA
9.5 48 reviews
Chatham, MA
15/08 – 22/08
£2365/nighttotal: £16555 (7 )

Heated Pool Ac 1/2 Mile To Beach!

8 10
apartment , Harwich
This South Harwich holiday home boasts an excellent location, less than 1.6km from Red River Beach and Cape Cod Beaches, and within 3.2km of Forest Beach and Harwich Port.
This eight-bedroom property offers 278 square metres of space, including a private pool, fully equipped kitchen, laundry facilities, and parking, perfect for large families or groups seeking a relaxing seaside escape.
Walk 2beach, Pool, Hot Tub, Gameroom, Petsok - Chatham, MA
9.8 41 reviews
Chatham, MA
15/08 – 22/08
£1885/nighttotal: £13195 (7 )

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

1 10
apartment , Chatham
This stunning four-bedroom Chatham holiday home is situated near Hardings Beach, a short walk from the shore and close to paddleboard rentals and walking trails.
The property boasts four bathrooms, a private pool and hot tub, a fully equipped outdoor kitchen, an indoor game room, a movie room, and a fire pit, comfortably accommodating up to ten guests.
Have It All! Beach, Town, & Pool - Chatham, MA
Chatham, MA
15/08 – 22/08
£3150/nighttotal: £22050 (7 )

Have It All! Beach, Town, & Pool

1 10
apartment , Chatham
This Chatham estate, near the headwaters of Upper Mill Pond and Mitchell River, is within walking distance of Chatham's town centre and Lighthouse Beach.
Sleeping up to 16 guests, this seven-bedroom, six-bathroom property comprises a main house and guest cottage, boasting a swimming pool, fitness centre, and ample parking, ideal for large family gatherings or multi-family holidays.

Frequently asked questions about holiday rentals in Chatham, MA

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

    Chatham has many beautiful walking and cycling routes. The Chatham Coastal Trail is a great option for a scenic walk or bike ride. It follows the coastline and offers stunning views of the ocean. If you're looking for a shorter walk, the Chatham Light Beach Trail is a nice option, leading to the Chatham Lighthouse.
  • 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.

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

    Chatham is a great place for outdoor activities. You can go swimming, sunbathing, or surfing at one of the many beaches. You can also go kayaking, paddleboarding, or windsurfing in the harbour. There are also plenty of opportunities for hiking and biking in the surrounding area.
  • 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 other towns or cities can be easily accessed from Chatham, MA?

    Chatham is well-connected to other towns and cities on Cape Cod. You can easily drive to nearby towns like Harwich Port, Dennis Port, and Orleans. If you want to explore further afield, you can take a ferry to Nantucket or Martha's Vineyard.
  • What are the best holiday rentals with a pool in Chatham, MA?

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

    Vacation rentals in Chatham typically offer a range of amenities, including kitchens, bathrooms, bedrooms, living rooms, and outdoor spaces. Many rentals also have access to swimming pools, hot tubs, and other recreational facilities.
  • What are the best rentals for families and kids 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 most popular time to visit, but it can be crowded and expensive. Spring and autumn offer more moderate temperatures and fewer crowds. Winter can be a great time to visit if you enjoy the peace and quiet.
  • What are the best rentals or Airbnbs with a jacuzzi in Chatham, MA?

  • What are the local dishes in Chatham, MA region?

    Chatham's local cuisine is heavily influenced by its proximity to the ocean. You can find fresh seafood dishes like lobster rolls, clam chowder, and fish and chips. There are also many restaurants that serve traditional New England dishes like clam bake and Yankee pot roast.

Destinations nearby

Best Chatham, MA holiday rentals with a balcony

Waterfront Home With Lovely Lake Views, Great Deck, Sun Porch & Fireplace - Chatham, MA
10 1 review
Chatham, MA
15/08 – 22/08
£644/nighttotal: £4508 (7 )

Waterfront Home With Lovely Lake Views, Great Deck, Sun Porch & Fireplace

3 10
apartment , Chatham
This waterfront property in South Chatham offers direct access to Mill Pond with scenic views, and is located 6 kilometres east of downtown Chatham, 1.6 kilometres from Hawksnest State Park, 3.2 kilometres from the Old Colony Rail Trail, and 4.8 kilometres from Forest Beach and Ridgevale Beach.
This spacious 193 square metre residence, ideal for up to 10 guests, features an open layout, a sun porch, an eat-in kitchen, a living room with a 60-inch HDTV, three bedrooms, central air conditioning, a washer/dryer, complimentary WiFi, and a lake-facing deck with a gas grill.
Walk To Dennisport Beaches 4 Min.bars And Restaurants 2min Walk.perfect Location - Chatham, MA
9.6 78 reviews
Chatham, MA
04/08 – 08/08
£376/nighttotal: £1504 (4 )

Walk To Dennisport Beaches 4 Min.bars And Restaurants 2min Walk.perfect Location

1 2
apartment , Dennis
This apartment is located near the beach in Dennis, within a 10-minute walk of Sea Street Beach and Cape Cod Beaches, and within 2 miles of the Cape Cod Theatre Company and Swan Pond River. The property has received excellent ratings for user experience, location, and cleanliness.
The apartment is a one-bedroom, one-bathroom property with a floor area of 56 square meters. Guests can enjoy a fully equipped kitchen, internet access, and a terrace or balcony, as well as parking, a garden, and a range of other amenities.
Beautifully Renovated W/ Access To Beach! - Chatham, MA
9.9 91 reviews
Chatham, MA
15/08 – 22/08
£1314/nighttotal: £9198 (7 )

Beautifully Renovated W/ Access To Beach!

6 10
apartment , Chatham
This Chatham house is located just a 2.4 kilometre walk from the Chatham Shark Center and Cape Cod Beaches, and a 3.2 kilometre drive from Fox Hill and Chatham Fish Pier, making it a great base for exploring the area. The property has excellent user, location and cleanliness ratings.
The house has 4 bathrooms and is 325 square metres in size. It features a fully equipped kitchen, garden, terrace, air conditioning, parking and free Wi-Fi, as well as a washing machine, coffee/tea maker, and a TV.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.3 2671 reviews
Chatham, MA
04/08 – 08/08
£472/nighttotal: £1888 (4 )

The Mansion At Ocean Edge Resort & Golf Club

1 2
resort , Brewster
The Mansion at Ocean Edge Resort and Golf Club is located in Brewster, a short drive from the Cape Cod Museum of Natural History and the Wellfleet Drive-In Theater & Cinemas. It has consistently received very good ratings for location, cleanliness, and overall user experience.
The resort offers a range of accommodation options, including guest rooms with patios or balconies and villas with full kitchens and living rooms. Guests can enjoy a private beach, two swimming pools, a spa, a fitness centre, tennis courts, and a variety of dining options, including a pub, a tavern, and a seasonal terrace.

Top-Rated Self-Catering Holiday Rentals with Free Parking in Chatham, MA

Parking is sorted from the start as these holiday rentals near the water in Chatham, MA include free on-site spaces.

Inn On The Beach - Chatham, MA
8.9 56 reviews
Chatham, MA
04/08 – 08/08
£501/nighttotal: £2004 (4 )

Inn On The Beach

1 2
resort , Harwich
The Inn On The Beach is located in Harwich Port, a 32km drive from Nickerson State Park, offering a peaceful escape on the Cape Cod coast. The property receives consistently high ratings for its cleanliness, location, and overall experience.
The hotel offers a range of comfortable rooms with amenities like a microwave, refrigerator, patio, and cable TV. Guests can enjoy a continental breakfast, free Wi-Fi, and direct access to a private beach with lounge chairs, hammocks, and beach umbrellas.
Steps2beach &Rail Trail | Blueberry Pond Sanctuary - Chatham, MA
Chatham, MA
09/07 – 13/07
£716/nighttotal: £2864 (4 )

Steps2beach &Rail Trail | Blueberry Pond Sanctuary

5 6
apartment , Brewster
This five-bedroom, three-bathroom detached house in Brewster offers immediate access to the Cape Cod Rail Trail, Nickerson State Park, and Blueberry Pond, with bay beaches such as Breakwater Beach and Paine's Creek just minutes away.
This property boasts a spacious 0.7-acre private garden with a fire pit and Adirondack chairs, a jacuzzi tub in the master en-suite, an outdoor shower, and an open-plan upper-level living, dining, and kitchen space with vaulted ceilings and a gas fireplace, accommodating up to six guests.
Driftwood - Har - Ed13 - Chatham, MA
Chatham, MA
07/08 – 14/08
£765/nighttotal: £5355 (7 )

Driftwood - Har - Ed13

1 7
house , Harwich
This Harwich holiday cottage offers a convenient base, situated 21-24 kilometres from Nauset Lighthouse and the Cape Cod National Seashore, with Wellfleet Bay Wildlife Sanctuary also 22 kilometres away.
This property accommodates up to 15 guests across 4 bedrooms and features a fully equipped kitchen with a dishwasher and oven, air conditioning, private parking, and complimentary WiFi, ideal for exploring the Cape.
Dennis Family Oasis: Pool, Hot Tub, & Fire Pit! - Chatham, MA
Chatham, MA
04/08 – 08/08
£3654/nighttotal: £14616 (4 )

Dennis Family Oasis: Pool, Hot Tub, & Fire Pit!

1 2
apartment , Dennis
This Dennis Retreat is a six-bedroom, five-bathroom residence located in South Dennis, offering convenient access to Hyannis Harbour, Cape Cod's beaches, and Mayflower Beach, all within a few kilometres.
This property provides accommodation for up to 10 guests, featuring a heated swimming pool, spa, sauna, and a firepit, alongside amenities such as air conditioning, a microwave oven, and a dishwasher, with parking included for your convenience.
©2026 cozycozy.com