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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
Located in Mashpee, this cottage is by the ocean, a 2-minute drive from South Cape Beach and 6 minutes from Popponesset Beach.
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
The price is AU$1,397 per night from 21 May to 22 May
AU$1,397
includes taxes & fees
21 May - 22 May
When you stay at this cottage in Mashpee, you'll be on the beach, within a 5-minute drive of South Cape Beach and South Cape Beach State Park.
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
Located in Mashpee, this cottage is by the sea, a 2-minute drive from South Cape Beach and 6 minutes from South Cape Beach State Park.
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
With a stay at this cottage in Mashpee, you'll be by the sea, just steps from Popponesset Beach and a 5-minute drive from 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
Located in Mattapoisett, this cottage is a 3-minute drive from Nasketucket Bay State Reservation and 10 minutes from Wings & Things.
Oceanside Cottage with Private Beach
2-bdrm Cottage | Close to Everything | Pet Friendly

2-bdrm Cottage | Close to Everything | Pet Friendly

Falmouth
With a stay at this cottage in East Falmouth, you'll be on the waterfront, within a 10-minute drive of Cape Cod Beaches and Cape Cod Country Club.
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
With a stay at this cottage in Mashpee, you'll be within a 10-minute drive of Cape Cod Beaches and Cape Cod Children's Museum.
★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
Located in Edgartown, this cottage is by the sea, within a 10-minute drive of Mytoi Garden and Chappaquidick Dike Bridge.
Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability
12 VINEYARD VIEW - FULLY RENOVATED

12 VINEYARD VIEW - FULLY RENOVATED

mashpee
When you stay at this cottage in Mashpee, you'll be near the beach and 12 minutes by foot from South Cape Beach.
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
155 Cottages
Lowest Price
AU$190
Highest Price
AU$1,397
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
Located in Chilmark, this vacation home is by the sea, within a 5-minute drive of Waskosim's Rock Reservation and Middle Road Sanctuary.
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 AU$301 per night from 7 May to 8 May
AU$301
includes taxes & fees
7 May - 8 May
When you stay at Sea Crest Beach Resort in North Falmouth, you'll be near the bay, just steps from Cape Cod Beaches and Old Silver Beach.
Sea Crest Beach Resort
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 8 May to 9 May
AU$190
includes taxes & fees
8 May - 9 May
Located in Falmouth, Iris Hotel Cape Cod is on a lake, a 2-minute drive from Island Queen Ferry and 5 minutes from Cape Cod Beaches.
Iris Hotel Cape Cod
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Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is AU$331 per night from 4 May to 5 May
AU$331
includes taxes & fees
4 May - 5 May
When you stay at Summercamp in Oak Bluffs, you'll be near the beach, just steps from Cottage Museum and 4 minutes by foot from Oak Bluffs Ferry Terminal.
Summercamp
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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.