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Brewster, MA cottages
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48 Cottages at the best price in Brewster, MA

Our Favourite Family-Friendly Cottages in Brewster, MA

Choosing a family-friendly cottage in Brewster, MA ensures a perfectly tailored, stress-free holiday for all ages.

Beachfront Cute Cottage On Private  Beach. Best View On The Cape.  On High Bluff - Brewster, MA
10 8 reviews

Beachfront Cute Cottage On Private Beach. Best View On The Cape. On High Bluff

cottage, Brewster
This 2-bedroom beach house in Brewster, MA, offers direct access to a private beach on a cliff with exceptional bay sunsets, and is conveniently located near the wider Cape Cod Beaches.
The property sleeps four guests and features a fully equipped kitchen, air conditioning, Wi-Fi, and an outdoor shower, with a porch area suitable for work or creative pursuits.
Private Beach.  Fabulous Bay Views. Wifi - Brewster, MA
No reviews

Private Beach. Fabulous Bay Views. Wifi

cottage, Brewster
This Brewster holiday let offers direct access to a 109-metre private beach and boasts unparalleled panoramic views of Cape Cod Bay, the Sagamore Bridge, and Provincetown, situated at the highest point between the bridge and Truro.
This family-friendly holiday home accommodates four guests across two bedrooms, featuring a full kitchen, air conditioning, and a garden, with the Brewster flats, ideal for walking at low tide, located nearby, and Hyannis Harbour approximately 16 kilometres away.
47 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Brewster, MA
No reviews

47 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Harwich
This detached property is situated in the Wychmere Village community, 800 metres from Red River Beach on Nantucket Sound and within 1.6 kilometres of Harwich Port's shops and restaurants.
This two-bedroom bungalow offers accommodation for four guests, featuring a private deck with a grill and outdoor shower, air conditioning, a swimming pool, and a fitness centre, all within the Wychmere Village community.

Best Brewster, MA cottages with a garden

Cape Charm! Sandy Toes Just Steps From Beach - Brewster, MA
9.0 9 reviews

Cape Charm! Sandy Toes Just Steps From Beach

cottage, Dennis
This Dennis Port holiday home is conveniently located a short walk from Cape Cod Beaches and Sea Street Beach, and within 3.2 kilometres of the Cape Cod Theatre Company and Pleasant Road Beach.
This 67 square metre self-catering property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, swimming pool, spa, tennis court, and free Wi-Fi.
Pond Front Beach Pet Friendly Ac Wifi - Brewster, MA
9.2 28 reviews

Pond Front Beach Pet Friendly Ac Wifi

cottage, Harwich
This charming cottage sits on a peaceful pond in Harwich, just over 1.5km from Dunkin' Donuts and the Harwich Public Market, offering a tranquil escape from the hustle and bustle of town. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and convenient stay.
The two-bedroom cottage, spanning 59 square metres, comfortably accommodates up to four guests. The property boasts a modern kitchen, a private garden, a spa, and a range of other amenities, including a keyless entry system, making it ideal for relaxing and exploring the local area.
New For 2026! 1/2 Mile To Swan Pond (2414) - Brewster, MA
No reviews

New For 2026! 1/2 Mile To Swan Pond (2414)

cottage, Dennis
This Dennis Port seaside cottage, an 8-minute (approximately 13 km) drive from Cape Cod Beaches and Sea Street Beach, offers stunning ocean views.
The 76 square metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, in-unit laundry, a garden with barbecue, free parking, Wi-Fi, and air conditioning.
Cloud 9 - Community Pool-walk To Beach-private - Brewster, MA
10 2 reviews

Cloud 9 - Community Pool-walk To Beach-private

cottage, Harwich Port
This Harwich Port holiday home is located 800 metres from Red River Beach and within 1.6 kilometres of Harwich Port's shops and restaurants, with ferries to Nantucket and Monomoy Island also nearby.
This two-bedroom bungalow accommodates up to four guests and features a private fenced-in garden with outdoor dining, an enclosed outdoor shower, and access to a seasonal community swimming pool, alongside complimentary daily Xplorie tickets for local attractions.

Frequently asked questions about cottages in Brewster, MA

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Check Out Cottages with a Hot Tub in Brewster, MA

Unwind after a coastal adventure with a private hot tub soak at your Brewster, MA cottage.

Private Cottage Tucked Close To Beaches And Town (2412) - Brewster, MA
No reviews

Private Cottage Tucked Close To Beaches And Town (2412)

cottage, Dennis
This Dennis Port holiday home is situated at the end of a quiet cul-de-sac, a short drive from beaches and attractions such as the Cape Cod Theatre Company and Whydah Pirate Museum.
The single-storey property sleeps six, featuring an open-plan kitchen, dining and living area, one bedroom, a loft with two queen beds, a garden, on-site parking, and a washer/dryer; kayaking and paddleboarding are easily accessible from a nearby town landing.

Search Dog-Friendly Holiday Cottages in Brewster, MA

Book a dog-friendly cottage in Brewster, MA for a relaxing break that welcomes the whole family.

Charming 2-bedroom Cottage In Fabulous Harwich With Wifi, Ac - Brewster, MA
9.0 6 reviews

Charming 2-bedroom Cottage In Fabulous Harwich With Wifi, Ac

cottage, Harwich
This two-bedroom Harwich holiday home is situated in Northwest Harwich, offering easy access to attractions such as Cape Cod Baseball & Bumper Boats and Cape Cod Lavender Farm (distances to these attractions require further clarification).
Sleeping up to 10 guests, the property features two bathrooms, Wi-Fi, air conditioning, and is pet-friendly; further details on proximity to Hyannis Harbour, West Dennis Beach, and Mayflower Beach (distances unspecified) are needed.
59 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Brewster, MA
9.3 20 reviews

59 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Harwich
This Harwich holiday home is situated on a secluded lane near Aunt Edie's Pond, approximately 1.8km from a Dunkin' Donuts and 2.4km from Harwich Public Market, offering tranquil waterfront access with swimming and kayaking.
The 59 square metre property sleeps four in two bedrooms and one bathroom, boasting a newly renovated interior, spa, fitness centre, a screened porch, spacious deck with gas grill, and includes the Xplorie offer with £600 worth of local attraction tickets.
Renovated Chatham Cottage  Steps To Beach - Brewster, MA
8.6 24 reviews

Renovated Chatham Cottage Steps To Beach

cottage, Chatham
This newly renovated holiday home in South Chatham offers proximity to Nantucket Sound beaches, located just 150 metres away, and is within walking distance of South Chatham village, tennis courts, and the Cape Cod Rail Trail.
This 98 square metre property, accommodating up to 8 guests, features 3 bedrooms, 1 bathroom, air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher, and a private garden with a gas grill and patio.
Pond Front Beach Pet Friendly Ac Wifi - Brewster, MA
9.2 28 reviews

Pond Front Beach Pet Friendly Ac Wifi

cottage, Harwich
This charming cottage sits on a peaceful pond in Harwich, just over 1.5km from Dunkin' Donuts and the Harwich Public Market, offering a tranquil escape from the hustle and bustle of town. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and convenient stay.
The two-bedroom cottage, spanning 59 square metres, comfortably accommodates up to four guests. The property boasts a modern kitchen, a private garden, a spa, and a range of other amenities, including a keyless entry system, making it ideal for relaxing and exploring the local area.

Find the Best Seaside Cottages in Brewster, MA

Book a relaxing maritime vacation at comfortable coastal cottages in Brewster, MA situated near the shore.

Waterfront On Long Pond And Black Pond! - Brewster, MA
10 2 reviews

Waterfront On Long Pond And Black Pond!

cottage, Brewster

Popular 5-Star Holiday Cottages in Brewster, MA

Indulge in 5-star refinement and boutique styling at our premier luxury cottages across Brewster, MA.

59 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Brewster, MA
9.3 20 reviews

59 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Harwich

Choose the Right Cottages with a Pool in Brewster, MA

A cottage in Brewster, MA with a pool offers a heated dip right alongside the beach.

Waterfront On Long Pond And Black Pond! - Brewster, MA
10 2 reviews

Waterfront On Long Pond And Black Pond!

cottage, Brewster

Top Holiday Cottages with Free Parking in Brewster, MA

Enjoy hassle-free coastal trips with private parking at your cottage in Brewster, MA, avoiding any extra faff.

Waterfront On Long Pond And Black Pond! - Brewster, MA
10 2 reviews

Waterfront On Long Pond And Black Pond!

cottage, Brewster

Explore Holiday Cottages with Spa Facilities in Brewster, MA

Integrating wellness into your holiday is simple with a spa-equipped cottage waiting for you in Brewster, MA.

Walk To Private Beach, Central Air, Wifi, 3 Bedrooms. - Brewster, MA
9.8 56 reviews

Walk To Private Beach, Central Air, Wifi, 3 Bedrooms.

cottage, Chatham
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