A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Find Romantic Hotels in Chatham, MA

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Check availability on Chatham Romantic Hotels

Tonight
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chatham romantic hotels

A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
A garden with a pergola structure, a pathway, and a seating area.
A living room with wicker furniture, a fireplace, and a staircase.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.

1. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
Canada
Ashley
NT$5,718
NT$7,932 total
includes taxes & fees
Nov 8 - Nov 9
Chatham Wayside Inn
A pathway leading to a beach with boats in the background and a building with a tower.
A hotel entrance with a sign reading "Chatham Bars Inn Cape Cod".
An aerial view of a beach with rows of sunbeds and umbrellas, a pier extending into the water, and a small building near the beach.
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.

2. Chatham Bars Inn

Chatham Bars Inn
Chatham
United States
Yousuf Hussain
NT$11,345
NT$12,984 total
includes taxes & fees
Nov 12 - Nov 13
Chatham Bars Inn
A house with a brick exterior, white exterior walls, and a front porch with white chairs.
A beach with a fallen tree, clear blue water, and a forested shoreline.
A bedroom with a bed, a nightstand, a lamp, a window with curtains, a hat, and a magazine on the bed.
An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.

3. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
United States
Ian
NT$7,434
NT$8,508 total
includes taxes & fees
Oct 20 - Oct 21
Chatham Seafarer Inn
A sandy beach path with wooden fencing, leading to the ocean.
An outdoor patio with a fire feature, wicker furniture, and hanging flower baskets.
A sign for The Old Harbor Inn with a number 22 on the building.
A two-story house with a covered porch, a well-maintained garden, and a driveway.

4. Old Harbor Inn

Old Harbor Inn
Chatham
United States
Adélaïde
NT$13,755
NT$15,743 total
includes taxes & fees
Oct 25 - Oct 26
Old Harbor Inn
A room with a bed, two wicker chairs, a small table, a coffee maker, and a view of the sea through a window.
A white bicycle with brown tires parked outside a building with a wooden exterior.
A modern kitchen with white cabinets, a built-in oven, and a view of the ocean through large windows.
A room with a large window overlooking the sea, a white desk, and nautical-themed decor.

5. Chatham Tides

Chatham Tides
South Chatham
United States
Anthony
NT$5,181
NT$5,930 total
includes taxes & fees
Nov 10 - Nov 11
Chatham Tides
A hotel room with two beds, a desk with a television, a red chair, and a window with green curtains.
A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.
A compact living space with a dining area, kitchenette, and a television.
A breakfast buffet with pastries, a lamp, and storage containers on a wooden table.

6. Skaket Beach Motel

Skaket Beach Motel
Orleans
United States
Wayne
NT$4,150
NT$4,750 total
includes taxes & fees
Oct 19 - Oct 20
Skaket Beach Motel
An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.
A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.
A modern kitchen with a large island, wooden cabinets, a white refrigerator, and pendant lighting.
A golf course with sand bunkers, trees, and a clear blue sky.

7. The Villages at Ocean Edge

The Villages at Ocean Edge
Brewster
United States
Myunghee
NT$3,226
NT$5,164 total
includes taxes & fees
Nov 8 - Nov 9
The Villages at Ocean Edge
A balcony with a view of a beach, a table with a vase of flowers, and a chair.
A two-story building with a sign reading "Winston Inn and Boardwalk."
Two blue Adirondack chairs facing a sunset over a beach with a fence and vegetation in the foreground.
A spacious living room with a large window, a ceiling fan, and a glass coffee table with flowers.

8. Winstead Beach Resort

Winstead Beach Resort
Harwich Port
United States
William
NT$9,528
NT$10,905 total
includes taxes & fees
Oct 17 - Oct 18
Winstead Beach Resort
View all properties

Top Chatham Hotel Reviews

Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"The place was clean. The smell from the sea weed cleanup was potent."
Lewis 3-night trip
Posted 11 hours ago
Red Jacket Beach Resort
Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"We liked everything. The service was amazing and the resort is beautiful."
Linda 3-night trip
Posted 16 hours ago
Chatham Bars Inn

Frequently asked questions

Searching for romantic hotels in Chatham?
If you and your partner need a romantic vacation, we'd like to help you plan for it. Our guests also enjoy Chatham for its seafood restaurants and seaside. You might consider checking out some of the nearby sights and attractions such as Chatham Lighthouse, Chatham Lighthouse Beach, or Ridgevale Beach. If you're interested in staying near a particular destination, you can sort by neighborhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Chatham?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chatham: The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chatham is 54 inches.
What is there to do in Chatham?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out all there is to see and do in Chatham. If you and your love want to take in the area's natural beauty, you'll enjoy Chatham for its beautiful beaches. You might think about visiting Chatham Lighthouse, Chatham Lighthouse Beach, or Ridgevale Beach.
What's the best way to get to Chatham and around town during my romantic getaway?
This information about transportation options in Chatham might help your romantic trip go off without a hitch: The closest major airport is Hyannis, MA (HYA-Barnstable Municipal), located 16.8 mi (27 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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