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Featured Cottages in Chilmark

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

Mashpee
Stay at this cottage in Mashpee. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Popponesset Beach and South Cape Beach State Park ...
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.

New Rental - 2 bedrooms, 1.5 baths, with magnificent views.

Mashpee
Book a stay at this beach cottage in Mashpee. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Popponesset Beach and South Cape Beach State ...
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Mashpee
Stay at this cottage in Mashpee. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Popponesset Beach and South Cape Beach ...
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
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Adorable, 2 Bedroom Beach Cottage, Sleeps 4, private beach-Wilsons Grove

Adorable, 2 Bedroom Beach Cottage, Sleeps 4, private beach-Wilsons Grove

Mashpee
Stay at this cottage in Mashpee. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Popponesset Beach and Cape Cod Children's Museum ...
Adorable, 2 Bedroom Beach Cottage, Sleeps 4, private beach-Wilsons Grove
Oceanside Cottage with Private Beach

Oceanside Cottage with Private Beach

Mattapoisett
Stay at this cottage in Mattapoisett. Enjoy air conditioning. Popular attractions Nasketucket Bay State Reservation and West Island are located nearby.
Oceanside Cottage with Private Beach
2-bdrm Cottage | Close to Everything | Pet Friendly

2-bdrm Cottage | Close to Everything | Pet Friendly

Falmouth
Stay at this cottage in East Falmouth. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Falmouth Country Club and Cape Cod Country ...
2-bdrm Cottage | Close to Everything | Pet Friendly
★The Islander | Steps From Water, Fire Pit, AC★

★The Islander | Steps From Water, Fire Pit, AC★

Mashpee
Stay at this cottage in Mashpee. Enjoy free WiFi, a water park, and a garden. Popular attractions South Cape Beach State Park and Waquoit Bay National Estuarine ...
★The Islander | Steps From Water, Fire Pit, AC★
Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability

Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability

Edgartown
Stay at this cottage in Edgartown. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Mytoi Garden and Edgartown ...
Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability
12 VINEYARD VIEW - FULLY RENOVATED

12 VINEYARD VIEW - FULLY RENOVATED

mashpee
Stay at this cottage in Mashpee. Enjoy free WiFi, a water park, and patios. Popular attractions Popponesset Beach and South Cape Beach State Park are located ...
12 VINEYARD VIEW - FULLY RENOVATED
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chilmark Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Chilmark will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Chilmark definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Chilmark, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Chilmark Cottages essential information

Accommodation
146 Cottages
Lowest Price
NZ$227
Highest Price
NZ$371
Popular accommodation
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace, New Rental - 2 bedrooms, 1.5 baths, with magnificent views., Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach, Adorable, 2 Bedroom Beach Cottage, Sleeps 4, private beach-Wilsons Grove, Oceanside Cottage with Private Beach, 2-bdrm Cottage | Close to Everything | Pet Friendly, ★The Islander | Steps From Water, Fire Pit, AC★, Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability, 12 VINEYARD VIEW - FULLY RENOVATED

Top trending hotels in Chilmark

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Chilmark
Book a stay at this family-friendly vacation home in Chilmark. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Waskosim's Rock Reservation ...
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd, North Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$371 per night from 16 Apr to 17 Apr
NZ$371
includes taxes & fees
16 Apr - 17 Apr
Stay at this 3.5-star beach hotel in North Falmouth. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Sea Crest Beach Resort
Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

3 out of 5
51 Teaticket Highway, East Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$227 per night from 9 Apr to 10 Apr
NZ$227
includes taxes & fees
9 Apr - 10 Apr
Stay at this 3-star business-friendly hotel in East Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Admiralty Inn & Suites - a Red Collection Hotel
Save an average of 15% on thousands of hotels when you're signed in
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is NZ$350 per night from 18 Apr to 19 Apr
NZ$350
includes taxes & fees
18 Apr - 19 Apr
Stay at this 3.5-star beach hotel in Oak Bluffs. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the ...
Summercamp
Don't see what you're looking for?
See all available properties in Chilmark
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.