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

143 M² House ∙ 3 Bedrooms ∙ 8 Guests - Chatham, MA
10 1 review
Chatham, MA
07/08 – 14/08
SG$2015/nighttotal: SG$14105 (7 )

143 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 7
house , Chatham
This Chatham holiday home is situated in a peaceful neighbourhood, 0.8km from Chatham Lighthouse, 2.1km from Chatham town centre, and a short walk to Lighthouse Beach and Outermost Harbour.
The 142 square metre property boasts three ensuite bedrooms sleeping eight, a spacious wraparound deck with ocean views, and amenities including a gas grill, fire pit, and Xplorie's free local attraction tickets offer.
Charming Second-floor Retreat With A Full Kitchen And Balcony View - Chatham, MA
9.2 37 reviews
Chatham, MA
15/07 – 17/07
SG$1057/nighttotal: SG$2114 (2 )

Charming Second-floor Retreat With A Full Kitchen And Balcony View

2 2
apartment , Brewster
This apartment is situated within the historic town of Brewster, offering a prime location on Cape Cod, 2.3 kilometres from Ellis Landing Beach and 29 kilometres from the National Seashore, with Provincetown 51 kilometres away.
This 88-square-metre flat features two bedrooms and two bathrooms, accommodating up to six guests with an open-concept living and kitchen area, air conditioning, a swimming pool, and access to resort amenities.
Compound On Historic Bank St Near Wychmere Club - Chatham, MA
10 39 reviews
Chatham, MA
09/07 – 13/07
SG$4151/nighttotal: SG$16604 (4 )

Compound On Historic Bank St Near Wychmere Club

7 6
apartment , Harwich
This three-bedroom Harwich Port holiday home is situated on historic Bank Street, a short walk or cycle ride (less than 1km) from Bank Street Beach, Saquatucket Harbour, and the Wychmere Beach Club.
The self-catering property boasts a modern kitchen with dishwasher, three parking spaces, a garden with firepit and outdoor shower, plus beach essentials and an open-plan living area with a games table and a second living area that can be used as a third bedroom.
Beachside Retreat! Cozy 1-bedroom W/ Private Yard - Chatham, MA
10 1 review
Chatham, MA
15/07 – 17/07
SG$901/nighttotal: SG$1802 (2 )

Beachside Retreat! Cozy 1-bedroom W/ Private Yard

1 2
apartment , Dennis
This Dennis beach house, a short walk from Haigis Beach and Sea Street Beach, offers easy access to Cape Cod's coastline and is under 3.2km from Swan Pond River and Bass River Lighthouse.
The 56 square metre property comprises one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private garden, patio, and free Wi-Fi.

Best Chatham, MA holiday rentals with a pool

Among the 1015 accommodations in Chatham, MA, here are the 4 best rentals with a pool

House ∙ 3 Bedrooms ∙ 8 Guests - Chatham, MA
9.6 5 reviews
Chatham, MA
07/08 – 14/08
SG$1154/nighttotal: SG$8078 (7 )

House ∙ 3 Bedrooms ∙ 8 Guests

3 7
house , Chatham
Azure Cottage, situated in Chatham's Oyster Pond area, is less than 1.6km from Chatham town centre and under 3.2km from Chatham's beaches.
This three-bedroom, two-bathroom property sleeps eight, boasts a private 0.6-hectare garden, hot tub, swimming pool, and fitness centre, plus a $750 Xplorie package offering free local attraction tickets.
Cozy Mid-cape Studio Steps To The Beach & Pool - Chatham, MA
10 6 reviews
Chatham, MA
15/07 – 17/07
SG$460/nighttotal: SG$920 (2 )

Cozy Mid-cape Studio Steps To The Beach & Pool

1 2
studio , Dennis
This Dennis, Massachusetts seaside apartment is located within a 1.6km walk of Haigis Beach and Sea Street Beach, and under 3.2km from Swan Pond River and Bass River Lighthouse.
The self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private patio, swimming pool, spa, and on-site water park.
Charming Studio Dennis Port Getaway With Wifi And Ac - Close To Beach! - Chatham, MA
9.6 4 reviews
Chatham, MA
15/07 – 17/07
SG$498/nighttotal: SG$996 (2 )

Charming Studio Dennis Port Getaway With Wifi And Ac - Close To Beach!

1 2
studio , Dennis
This Dennis Port apartment is conveniently located a mere 640 metres from Cape Cod Beaches and 1.3 kilometres from Sea Street Beach, offering easy access to coastal activities.
This studio apartment, measuring 19 square metres and accommodating two guests, features air conditioning, Wi-Fi, a kitchenette with a microwave and fridge, and access to a shared swimming pool and private terrace.
Chatham Bars Inn - Chatham, MA
9.1 1099 reviews
Chatham, MA
09/07 – 13/07
SG$9678/nighttotal: SG$38712 (4 )

Chatham Bars Inn

3 6
resort , Chatham
Chatham Bars Inn is an oceanfront hotel in Chatham, Massachusetts, a short distance from the Chatham Lighthouse and the Chatham Bars. The hotel consistently receives excellent ratings for its location, user experience, and cleanliness.
The hotel offers a range of rooms and suites, all featuring modern amenities. Guests can enjoy a variety of on-site amenities and activities, including a heated pool, private beach access, a full-service spa, and several restaurants.

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Best Chatham, MA holiday rentals with a balcony

Dog-friendly Beach Cottage On Harwich's Main Street With Large Lawn - Chatham, MA
Chatham, MA
15/07 – 17/07
SG$927/nighttotal: SG$1854 (2 )

Dog-friendly Beach Cottage On Harwich's Main Street With Large Lawn

2 2
apartment , Harwich
This apartment is located on Harwich's main street, 500 metres from the beach and 800 metres from Wychmere Beach Club, offering convenient access to amenities and local attractions.
This 67 square metre flat accommodates up to five guests in two bedrooms and one bathroom, featuring a full kitchen (no dishwasher), air conditioning, and a terrace, with a nearby garden area for outdoor activities.
Ideally Located Home With Yard, Grill, Bikes, Gas Fireplace, Streaming, W/d, Ac - Chatham, MA
9.6 10 reviews
Chatham, MA
15/07 – 17/07
SG$1322/nighttotal: SG$2644 (2 )

Ideally Located Home With Yard, Grill, Bikes, Gas Fireplace, Streaming, W/d, Ac

4 2
apartment , Brewster
This spacious apartment in West Brewster is a short drive from multiple beaches and situated near attractions such as the Cape Cod Museum of Natural History and Dennis Pines Golf Course.
Offering 167 square meters of living space for up to 8 guests, this property features four bedrooms, four bathrooms, a fully equipped kitchen with granite countertops and stainless steel appliances, and an expansive outdoor space with a patio, grill, and yard games.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.3 2767 reviews
Chatham, MA
04/08 – 08/08
SG$813/nighttotal: SG$3252 (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.
Harwich Getaway By Leavetown Vacations - Chatham, MA
Chatham, MA
25/06 – 27/06
SG$920/nighttotal: SG$1840 (2 )

Harwich Getaway By Leavetown Vacations

3 4
house , Harwich
This Harwich holiday home is situated approximately 26 kilometres from Nauset Lighthouse, 29 kilometres from Wellfleet Bay Wildlife Sanctuary, and 31 kilometres from Cape Cod National Seashore.
This spacious property boasts 663 square metres of floor area, offering three bedrooms, three bathrooms, and sleeps up to eleven guests, complete with a fully equipped kitchen, private garden, free Wi-Fi, parking, and an on-site restaurant.

Best Chatham, MA holiday rentals with parking

Door To Shore In A Hop, Skip, And A Jump! - Chatham, MA
9.9 58 reviews
Chatham, MA
01/07 – 06/07
SG$366/nighttotal: SG$1830 (5 )

Door To Shore In A Hop, Skip, And A Jump!

1 2
apartment , Harwich
This Harwich apartment, ideally located 0.5 km from Bank Street Beach and within walking distance of Main Street's shops and restaurants, offers easy access to Wychmere wedding venue (0.8 km).
The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen, private deck with bocce and cornhole, beach essentials, and free Wi-Fi; weekly cleaning is provided for stays of two weeks or more.
Slow M'ocean – A Fresh Take On Cape Calm - Chatham, MA
Chatham, MA
07/08 – 14/08
SG$2554/nighttotal: SG$17878 (7 )

Slow M'ocean – A Fresh Take On Cape Calm

1 7
house , Chatham
Slow M'Ocean, a one-bedroom house in Chatham, is a six-minute walk from Chatham Lighthouse Beach and within 27-30km of Nauset Lighthouse, Wellfleet Bay Wildlife Sanctuary, and Cape Cod National Seashore.
This pet-friendly property sleeps 15 guests, boasting four bathrooms, a fully equipped kitchen with dishwasher, air conditioning, cable TV, a fireplace, and internet access; nearby attractions include Chatham's town centre and Cape Cod Gateway Airport (30km).
Inn On The Beach - Chatham, MA
8.9 56 reviews
Chatham, MA
04/08 – 08/08
SG$863/nighttotal: SG$3452 (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.
Walk To Nantucket Sound Beaches! Family Getaway - Chatham, MA
Chatham, MA
15/07 – 17/07
SG$717/nighttotal: SG$1434 (2 )

Walk To Nantucket Sound Beaches! Family Getaway

3 2
house , Dennis
This Dennis Port holiday home is a short walk from Sea Street Beach, 34 kilometres from Nauset Lighthouse, and 37 kilometres from Heritage Museums & Gardens and Cape Cod National Seashore.
This detached property offers 56 square metres of living space with 3 bedrooms and 1 bathroom, accommodating up to 9 guests with air conditioning, a fully equipped kitchen, free private parking, and an outdoor dining area.
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