Holiday Rentals in Chatham, MA

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Chatham, MA holiday rentals
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Best Holiday rentals and Airbnb offers in Chatham, MA

Best family friendly Chatham, MA holiday rentals

Among the 1379 accommodations in Chatham, MA, here are the 4 best family friendly rentals

Chatham  Water  Front/view House First Time Rental - Chatham, MA
10 22 reviews

Chatham Water Front/view House First Time Rental

apartment, Chatham
This waterfront property in Chatham is just 1.5 miles from the town centre and a short walk from the Cape Cod Biking Trail, offering a peaceful escape from the hustle and bustle. The house has been consistently rated excellent by previous guests.
The property has three bedrooms, two bathrooms and can comfortably accommodate up to eight guests. It features a spacious deck overlooking the lake with a Weber grill, a family-friendly games room, and two kayaks for guests to enjoy.
Chatham Luxury Retreatporch, Art & Family Fun - Chatham, MA
10 1 review

Chatham Luxury Retreatporch, Art & Family Fun

apartment, Chatham
This Chatham seaside property is situated a short 2.4km walk from Hardings Beach and Cape Cod Beaches, and under 5km from Hardings Lighthouse and the Chatham Chamber of Commerce.
This 256 square metre house offers three bedrooms, four bathrooms, sleeps eight guests, and includes a fully equipped kitchen, private garden, terrace, parking, and access to on-site amenities such as a games room and barbecue grills.
4br+loft Beautiful Chatham-year Round-sleeps Up To 8 & 1 Mile To Town **Video** - Chatham, MA
9.8 58 reviews

4br+loft Beautiful Chatham-year Round-sleeps Up To 8 & 1 Mile To Town **Video**

apartment, Chatham
This North Chatham holiday home is situated near the sea, less than 1.6km from the Chatham Shark Center and Cape Cod beaches, and under 1.6km from the Chatham Marconi Maritime Center and Fox Hill.
This 195 square metre property boasts four bedrooms, four bathrooms, sleeps eight guests, and includes a fully equipped kitchen, spa, tennis court, and garden with barbecue facilities, offering a luxurious seaside escape.
214 M² House ∙ 1 Bedroom ∙ 8 Guests - Chatham, MA
9.8 11 reviews

214 M² House ∙ 1 Bedroom ∙ 8 Guests

house, Chatham
This Chatham holiday home is located in the Cockle Cove Beach area, approximately 1 kilometre from Cockle Cove Beach on Nantucket Sound and 0.5 kilometres from the Cape Cod Rail Trail.
The 213-square-metre property boasts a spacious open-plan layout, sleeping up to eight guests in one bedroom and a bonus room, and includes a fully equipped kitchen, spa, fitness centre, two-car garage, and enclosed outdoor shower.

Best Chatham, MA holiday rentals with a pool

Among the 1379 accommodations in Chatham, MA, here are the 4 best rentals with a pool

The Gables: 364-c  Chatham Resort Style Estate With Heated Pool, Close To Everything - Chatham, MA
10 15 reviews

The Gables: 364-c Chatham Resort Style Estate With Heated Pool, Close To Everything

apartment, Chatham
This Chatham resort is located just a short walk from the bustling Main Street and a 5-minute cycle to Lighthouse Beach, Chatham's largest beach. The property has received excellent user ratings, making it a popular choice for travellers.
This spacious villa covers 399 square metres and can comfortably accommodate 16 guests. The property features a heated pool, hot tub, gas fire pit, gas grill, outdoor kitchen, game room, and high-speed Wi-Fi, as well as a private garden and parking.
Sand Simeon - Relax, Unwind, Repeat!! - Chatham, MA
9.6 14 reviews

Sand Simeon - Relax, Unwind, Repeat!!

apartment, Chatham
This luxury home is located in the charming town of Chatham, just 0.3 kilometres from Lighthouse Beach and a short walk to Main Street. This property has received excellent reviews from previous guests.
This spacious six-bedroom home spans 474 square metres and can comfortably accommodate up to 14 guests. The home features a private pool, central air conditioning, a gourmet kitchen with professional appliances, a fireplace, a wet bar, multiple flat-screen TVs, a pool table, a media area, and a garden.
Relaxing Fairway Escape With Resort Pools, Club Access, & Steps To Arbor Pool - Chatham, MA
No reviews

Relaxing Fairway Escape With Resort Pools, Club Access, & Steps To Arbor Pool

apartment, Brewster
This spacious 139 square metre flat offers a prime location within Ocean Edge Resort, Brewster, directly on the 9th fairway and a 300-metre walk to the Arbor Pool and Ocean Edge shuttle stop for access to Crosby Landing Beach.
This family-friendly condo accommodates eight guests with three bedrooms and two bathrooms, featuring a kitchen with a fridge, microwave oven, and dishwasher, plus air conditioning, a swimming pool, jacuzzi, garden, sauna, and spa, with optional resort passes providing access to tennis, pickleball, bike rentals, kayaks, and paddleboards.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.3 2649 reviews

The Mansion At Ocean Edge Resort & Golf Club

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.

Frequently asked questions about holiday rentals in Chatham, MA

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Best Chatham, MA holiday rentals with a balcony

Adorable Condo With Patio, Shared Pool, & Hot Tub - Close To The Water - Chatham, MA
No reviews

Adorable Condo With Patio, Shared Pool, & Hot Tub - Close To The Water

apartment, Brewster
This Ocean Edge condo in Brewster, MA, is conveniently located near golf courses and beaches, offering easy access to the town beach and the wider Ocean Edge resort amenities.
This 102 square meter apartment accommodates up to six guests, featuring one bedroom, two bathrooms, a fully equipped kitchen, a patio with a gas grill, and access to resort facilities including swimming pools and a gym.
Peaceful Retreat On Chilton Lane - Chatham, MA
10 1 review

Peaceful Retreat On Chilton Lane

apartment, Brewster
This Brewster apartment is conveniently located near Cape Cod beaches and attractions such as the Cape Cod Inflatable Park, offering easy access to other Cape Cod destinations.
The 87-square-metre (936 square feet) self-catering flat features two bedrooms, two bathrooms, sleeps five, and includes a fully equipped kitchen, balcony, free Wi-Fi, a swimming pool, fitness centre, and concierge service; on-site amenities also include a water park, indoor pool, and hot tub.
Heated In-ground Pool And New Central Ac! - Chatham, MA
9.7 39 reviews

Heated In-ground Pool And New Central Ac!

apartment, Brewster
This five-bedroom house in Brewster is situated just 5 kilometres from Captains Golf Course and Ocean Edge Golf Club, offering easy access to both courses and the nearby attractions of Sheep Pond and Nickerson State Park.
The 232 square metre property features a private pool, a terrace, a garden and a fully equipped kitchen, comfortably accommodating up to 10 guests.
Cape Cod Villa - Chatham, MA
10 19 reviews

Cape Cod Villa

house, Harwich
This four-bedroom Harwich villa, situated 19 kilometres from the Nauset Lighthouse and offering easy access to local attractions, provides a luxurious family-friendly escape.
The 156 square metre property boasts a spa, private parking, a terrace, garden, and accommodates up to 12 guests, with amenities including a pool table, Wi-Fi, and a well-equipped kitchen.

Best Chatham, MA holiday rentals with parking

Water Front Private Beach - Chatham, MA
No reviews

Water Front Private Beach

apartment, Chatham
This waterfront flat in Chatham offers direct access to a private beach, situated a short distance from the town centre and its attractions.
This four-bedroom, three-and-a-half-bathroom apartment accommodates up to eight guests, featuring a kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and a garden.
Pet-friendly Cape Escape  6 Min To Beach - Chatham, MA
9.7 35 reviews

Pet-friendly Cape Escape 6 Min To Beach

apartment, Harwich
This pet-friendly house is located just 2.6 kilometres from Red River Beach, offering easy access to one of Harwich's most beautiful natural attractions. It boasts excellent ratings for location, cleanliness and user experience.
The spacious house has two bedrooms, comfortably accommodating up to five guests. Amenities include a fully equipped kitchen, a large deck with a gas grill, Wi-Fi, air conditioning, and an outdoor shower.
Walk To Beach/main Street/bike Path/dog Friendly - Chatham, MA
9.9 61 reviews

Walk To Beach/main Street/bike Path/dog Friendly

apartment, Chatham
This Chatham house, a 1.6km stroll from Chatham's beach and 1.9km from Main Street, provides easy access to the Wequossett Resort (4.8km away) and a local beach within a 15-minute walk.
The two-bedroom, one-bathroom property sleeps four, boasting a kitchen with dishwasher, air conditioning, a garden, parking for four cars, and an outdoor shower.
Delightful Chatham Cottage, Cheerful And Clean - Chatham, MA
9.7 161 reviews

Delightful Chatham Cottage, Cheerful And Clean

apartment, Chatham
This charming cottage is located just 3 kilometres from Chatham's bustling centre and less than 1.6 kilometres from the ocean and two sandy beaches, offering a peaceful retreat in a quiet, tree-lined neighbourhood. It consistently receives excellent ratings for location, cleanliness, and overall user experience.
The cottage provides comfortable accommodation for up to four guests, with one bedroom and one bathroom. It is equipped with a well-stocked kitchen, a sunny back deck, a private backyard, and amenities such as high-speed internet, cable TV, and games, ensuring a comfortable and enjoyable stay.
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