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Featured Cottages in Chilmark

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

2 out of 5
Mashpee
With a stay at this cottage in Mashpee, you'll be by the sea, within a 15-minute drive of Cape Cod Beaches and South Cape Beach.
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
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
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
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Cozy family-friendly cottage on beautiful Shining Sea bike trail

Cozy family-friendly cottage on beautiful Shining Sea bike trail

Falmouth
With a stay at this cottage in Falmouth, you'll be a 2-minute drive from Cape Cod Beaches and 7 minutes from Woods Hole Ferry Terminal.
Cozy family-friendly cottage on beautiful Shining Sea bike trail
LOCATION  & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

Tisbury
With a stay at this cottage in Vineyard Haven, you'll be by the sea, within a 15-minute drive of Inkwell Beach and Martha's Vineyard Chamber of Commerce.
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.

5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.

Mashpee
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.
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Tisbury
The price is AU$1,593 per night from 19 Aug to 20 Aug
AU$1,593
19 Aug - 20 Aug
includes taxes & fees
With a stay at this cottage, you'll be centrally located in Vineyard Haven, within a 10-minute drive of Inkwell Beach and Martha's Vineyard Chamber of ...
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Cozy Beach Cottage

Cozy Beach Cottage

Oak Bluffs
With a stay at this cottage, you'll be centrally located in Oak Bluffs, within a 5-minute drive of Inkwell Beach and Oak Bluffs Public Library.
Cozy Beach Cottage
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

Mashpee
With a stay at this cottage in Mashpee (Popponesset), you'll be steps from Popponesset Beach and a 5-minute drive from Cape Cod Children's Museum.
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
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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
153 Cottages
Lowest Price
AU$266
Highest Price
AU$1,593
Popular accommodation
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community, Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach, Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace, Cozy family-friendly cottage on beautiful Shining Sea bike trail, LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!, 5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views., Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site, Cozy Beach Cottage, Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

Top trending hotels in Chilmark

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Chilmark
When you stay at this vacation home in Chilmark, you'll be on the waterfront, within a 5-minute drive of Edys Island and Menemsha Beach.
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$266 per night from 2 Sept to 3 Sept
AU$266
2 Sept - 3 Sept
includes taxes & fees
With a stay at Falmouth Inn, you'll be centrally located in Falmouth, a 2-minute drive from Cape Cod Beaches and 10 minutes from Woods Hole Ferry Terminal.
Falmouth Inn
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$422 per night from 1 Sept to 2 Sept
AU$422
1 Sept - 2 Sept
includes taxes & fees
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
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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$331 per night from 2 Sept to 3 Sept
AU$331
2 Sept - 3 Sept
includes taxes & fees
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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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.