Get a free $100 with a gift card purchase of $350

Chilmark Bed and Breakfasts

Sort by:

Woods Hole Inn

Woods Hole, MA

Stay GREEN by the deep BLUE sea. Eco-travelers welcome at this newly restored historic property.

from $155

4.4 (40)
Accepts:

Visit Website

Woods Hole Inn

Woods Hole Inn

from $155

Woods Hole, MA

4.4 (40)

Visit Website

Palmer House Inn, The

Falmouth, MA

A romantic and historic B&B. Beaches, shops, and restaurants are a short stroll away.

from $169

4.5 (177)
Accepts:

Visit Website

Palmer House Inn, The

Palmer House Inn, The

from $169

Falmouth, MA

4.5 (177)

Visit Website

Woods Hole Passage Bed & Breakfast Inn

Falmouth, MA

This 100-year-old carriage house sits on nearly 2 acres of spacious grounds adorned by shade tree...

from $149

4.8 (8)

Visit Website

The Martha's Vineyard Resort

Oak Bluffs, MA

It's easy to see why the Martha's Vineyard Resort's guests are drawn to the charm and convivialit...

from $160

3.9 (32)

Check Dates

The Martha's Vineyard Resort

The Martha's Vineyard Resort

from $160

Oak Bluffs, MA

3.9 (32)

Visit Website »

Check Dates

The Madison Inn

Oak Bluffs, MA

Wonderfully affordable and superbly located in the heart of the village of Oak Bluffs on Martha's...

from $89

4.0 (1)

Visit Website

The Madison Inn

The Madison Inn

from $89

Oak Bluffs, MA

4.0 (1)

Visit Website

The Captain's Manor Inn

Falmouth, MA

A beautifully restored estate with 8 elegant guest rooms on 1.2 acres of park like grounds.

from $150

4.8 (19)

Visit Website

The Captain's Manor Inn

The Captain's Manor Inn

from $150

Falmouth, MA

4.8 (19)

Visit Website

Tivoli Inn

Oak Bluffs, MA

The Tivoli inn is a beautiful Victorian gingerbread house with lots of charm and a clean and frie...

from $85

4.5 (6)
Accepts:

Visit Website

Tivoli Inn

Tivoli Inn

from $85

Oak Bluffs, MA

4.5 (6)

Visit Website

Victorian Inn

Edgartown, MA

An attractive Inn with the casual elegance of a restored Whaling Captain's Home on the Island of ...

from $200

4.9 (3)

Visit Website

Victorian Inn

Victorian Inn

from $200

Edgartown, MA

4.9 (3)

Visit Website

Santuit Inn

Mashpee, MA

The Santuit Inn is an eighteen-unit boutique motel with a 2 bed cottage on Mashpee/Cotuit line

from $69

4.2 (1)

Check Dates

Santuit Inn

Santuit Inn

from $69

Mashpee, MA

4.2 (1)

Visit Website »

Check Dates

Captain Tom Lawrence House Bed and Breakfast Inn

Falmouth, MA

Historic Inn close to beaches and village shops and restauarants. Walk to ferry shuttle and bikeway

from $150

4.3 (27)

Visit Website

Get a free $100 with a gift card purchase of $350

Inn at Siders Lane

Falmouth, MA

"Elegant accommodations for those with discerning taste." This Falmouth inn is a Federal reprod...

from $150

4.7 (67)

Visit Website

Inn at Siders Lane

Inn at Siders Lane

from $150

Falmouth, MA

4.7 (67)

Visit Website

from $195

4.1 (37)
Accepts:

Check Dates

from $100

4.4 (12)

Visit Website

The Labyrinth House B&B and Massage

The Labyrinth House B&B and Massage

from $100

Cataumet, MA

4.4 (12)

Visit Website

The 1720 House

Vineyard Haven, MA

from $175

4.7 (44)

Visit Website

The 1720 House

The 1720 House

from $175

Vineyard Haven, MA

4.7 (44)

Visit Website

Crosby Hill Bed and Breakfast

Little Compton, RI

from $100

Visit Website

Crosby Hill Bed and Breakfast

Crosby Hill Bed and Breakfast

from $100

Little Compton, RI

Visit Website

Inn on the Sound

Falmouth, MA

from $145

4.9 (10)

Visit Website

Inn on the Sound

Inn on the Sound

from $145

Falmouth, MA

4.9 (10)

Visit Website

from $130

4.8 (21)
Accepts:

Check Dates

Nashua House

Oak Bluffs, MA

from $79

Visit Website

Nashua House

Nashua House

from $79

Oak Bluffs, MA

Visit Website

from $125

3.4 (2)

Visit Website

Vineyard Square Hotel & Suites

Vineyard Square Hotel & Suites

from $125

Edgartown, MA

3.4 (2)

Visit Website

Hanover House Inn

Vineyard Haven, MA

from $138

Accepts:

Visit Website

Hanover House Inn

Hanover House Inn

from $138

Vineyard Haven, MA

Visit Website

from $145

4.9 (29)
Accepts:

Visit Website

Captain David Kelley House on Cape Cod

Captain David Kelley House on Cape Cod

from $145

Centerville, MA

4.9 (29)

Visit Website

The Thorncroft Inn

Vineyard Haven, MA

from $195

Visit Website

The Thorncroft Inn

The Thorncroft Inn

from $195

Vineyard Haven, MA

Visit Website

Long Dell Inn on Cape Cod

Centerville, MA

from $150

4.8 (33)
Accepts:

Check Dates

Long Dell Inn on Cape Cod

Long Dell Inn on Cape Cod

from $150

Centerville, MA

4.8 (33)

Visit Website »

Check Dates

from $60

4.6 (13)
Accepts:

Mulberry Bed & Breakfast

Mulberry Bed & Breakfast

from $60

Wareham, MA

4.6 (13)

No results were found.

Your search was a little too specific.We suggest reducing the filters or searching for a different city.

Sponsored Links

Book a getaway today

Best Price Guarantee

We offer the Best Price Guarantee! Learn more

Recent reviews

Palmer House Inn, The

$169 - $299

4.6 (177)

"We have stayed at the Palmer House many times over the past 30 years... and with each..."

Read more...


The Blushing Oyster Bed & Breakfast

$165 - $230

4.8 (58)

"This rounded off our trip to New England, prior to going back to our son in NJ and th..."

Read more...


Yankee Clipper Inn

$129 - $389

4.2 (15)

"I just came back from my stay at the Yankee Clipper Inn. The weather was great and t..."

Read more...


View More Reviews

Chilmark B&B reviews

Overall rating:

The Chilmark B&B review score is based on feedback from travelers from around the world. See property page for full, detailed reviews by real travelers.

Top