A dock with boats, a small wooden structure, and a forested shoreline.

Find Romantic Hotels in Chilmark, MA from CA $621

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Check availability on Chilmark Romantic Hotels

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Chilmark romantic hotels

A spacious living area with a high ceiling, a dining table, and a kitchen area.
A bedroom with a bed, a desk, and a TV. There are three windows providing natural light.
A spacious room with a large wooden dining table, comfortable seating, and large windows offering a view of the outdoors.
A spacious living room with a brick fireplace, a large window, and a wooden coffee table.

1. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
United States
Collins E.
CA $700
CA $1,524 total
includes taxes & fees
Oct 19 - Oct 20
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A boat docked at a concrete pier with a sandy shore in the background.
A living room with a TV, couch, and wooden panel wall.
A residential driveway with two parked cars, a gravel path, and a wooden deck with potted plants.
A patio with wicker chairs and a small table, a grassy yard, a wooden fence, and a view of a body of water.

2. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
United States
Michele M.
CA $223
CA $621 total
includes taxes & fees
Oct 19 - Oct 20
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.
A living room with a large patterned rug, leather sofas, a dining table with chairs, and a flat-screen TV mounted on the wall.
A modern kitchen with white cabinets, stainless steel appliances, and a large island with seating.
A single-story house with a front porch, a well-maintained lawn, and a driveway.

3. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
United States
Stephanie B.
CA $255
CA $732 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A two-story house with a stone facade, a covered patio, and a well-maintained garden.
An outdoor patio area with a fire pit, seating, and a pool.
A swimming pool with a pergola and outdoor seating area.
A spacious living room with a fireplace, comfortable seating, and large windows.

4. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
United States
Lamar A.
Beautiful Estate with salt water pool & pond with kayaks
A spacious living area with wooden beams, a dining table, and a sofa.
A kitchen with white cabinets, a microwave, and a dining area with a round table and wooden chairs.
A spacious living area with a wooden staircase, a kitchen in the background, and a sign that reads "BEACH".
A wooden deck with a table and chairs, surrounded by lush greenery.

5. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
United States
Eric C.
CA $1,018
CA $1,660 total
includes taxes & fees
Oct 19 - Oct 20
The Seashell Cove - Martha's Vineyard
A water park with a large central pool, multiple slides, and a variety of play structures.
A living room with a brown sofa, a blue armchair, and a wooden coffee table.
A living room with a fireplace, a recliner, and a television on a mantel.
A patio with outdoor furniture, a tree, and a lattice fence.

6. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
United States
Jainessa
CA $403
CA $821 total
includes taxes & fees
Oct 31 - Nov 1
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A beach with clear water and a sandy shore.
A living room with a sofa, chairs, a coffee table, and a large window with a view of the outdoors.
A spacious living room with a staircase, a large window, and a variety of furniture including a sofa, a coffee table, and a side table.
A covered porch with a pergola, outdoor seating, and a view of a lake.

7. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
United States
cindy w.
CA $631
CA $1,473 total
includes taxes & fees
Oct 30 - Oct 31
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
View all properties

Top Chilmark Hotel Reviews

Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"Beautiful location! Our stay was just overnight so didn’t get to enjoy it to its fullest."
Thomas 1-night trip
Posted 2 days ago
Sea Crest Beach Resort
Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"The room was very clean."
Jamie 2-night trip
Posted 3 days ago
Admiralty Inn & Suites - a Red Collection Hotel
Faraway Martha's Vineyard

Faraway Martha's Vineyard

10/10 Excellent
"My stay was wonderful. The well-maintained and beautiful hotel had the best staff I’ve ever experienced!"
Krystin 2-night trip
Posted 3 days ago
Faraway Martha's Vineyard
Inn on the Square

Inn on the Square

10/10 Excellent
"Very helpful & friendly staff. Walkable to stores & Restaurants."
Dolores 1-night trip
Posted 4 days ago
Inn on the Square
The Coonamessett

The Coonamessett

8/10 Good
"Nice central location near Main Street restaurants, beaches and the shuttle to the MV ferry out of Woods Hole. Friendly and helpful staff. Plentiful free parking. It could use some capital improvements (rotting wood trim, missing roof shingles). Good value overall."
Andrew 2-night trip
Posted 4 days ago
The Coonamessett
Harbor View Hotel

Harbor View Hotel

10/10 Excellent
"Beautiful Hotel and Venue with impeccable amenities. Beautiful water views and outstanding and friendly Staff. Disappointed we were not able to stay longer. Will definitely plan another trip in the near future!"
Marc 1-night trip
Posted 9 days ago
Harbor View Hotel

Frequently asked questions

Searching for romantic hotels in Chilmark?
If you and your partner need some romantic time away, we've got just the thing. If you want to explore the area, you might head to Menemsha Beach, Chilmark Chocolates, or Edys Island. If you're interested in staying close to a particular destination, you can sort by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chilmark?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chilmark: The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chilmark is 50 inches.
What is there to do in Chilmark?
There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all there is to see and do in Chilmark. You might think about stopping by Menemsha Beach, Chilmark Chocolates, or Edys Island while you're seeing the sights.
What's the best way to get to Chilmark and around town during my romantic getaway?
These transportation options in Chilmark might help your romantic trip go off without a hitch: To get to Chilmark, book a flight to Vineyard Haven, MA (MVY-Martha's Vineyard), which is the closest major airport, located 7.6 mi (12.2 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

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