Find Romantic Hotels in Osterville, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Osterville Romantic Hotels

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Our top choices for Osterville romantic hotels

Exterior detail

Charming Antique Boathouse Located Directly On Long Pond.

Charming Antique Boathouse Located Directly On Long Pond.
Plymouth
9.8 out of 10, Exceptional, (112 reviews)
"The hosts were very accommodating. Our arrival was late, and it was easy to get into the boathouse."
United States
Mark P.
The price is AED 845
AED 1,338 total
includes taxes & fees
7 Jun - 8 Jun
Charming Antique Boathouse Located Directly On Long Pond.
Beach

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.6 out of 10, Exceptional, (113 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is AED 500
AED 1,211 total
includes taxes & fees
5 Jun - 6 Jun
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Property grounds

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is AED 1,102
AED 2,283 total
includes taxes & fees
26 May - 27 May
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Interior

Mariner Motor Lodge- "Where People Come By Choice And Not By Chance".

Mariner Motor Lodge- "Where People Come By Choice And Not By Chance".
Yarmouth
7.8 out of 10, Good, (16 reviews)
"Very convienent area to stay"
United States
ELISABETH R.
The price is AED 441
AED 727 total
includes taxes & fees
26 May - 27 May
Mariner Motor Lodge- "Where People Come By Choice And Not By Chance".
Terrace/patio

Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed

Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed
Bass River
10.0 out of 10, Exceptional, (108 reviews)
"Nice quiet neighborhood but close to a lot of different attractions. The home was perfect for our needs."
United States
Ryan T.
The price is AED 1,264
AED 3,136 total
includes taxes & fees
11 Jun - 12 Jun
Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed
Exterior

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (23 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is AED 889
AED 1,880 total
includes taxes & fees
26 May - 27 May
Spacious and Bright , Very Close to Beach!
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.0 out of 10, Wonderful, (4 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is AED 1,286
AED 3,282 total
includes taxes & fees
26 May - 27 May
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Marina

Edgartown Designer Cottage between Town & Beach.

Edgartown Designer Cottage between Town & Beach.
Katama
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful week in MV! The cottage had everything we needed and was a great location to bike into town or to the beach. Would love to come back and stay again!"
United States
Lauren B.
The price is AED 1,598
AED 2,884 total
includes taxes & fees
2 Jun - 3 Jun
Edgartown Designer Cottage between Town & Beach.
Interior

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
10.0 out of 10, Exceptional, (216 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
The price is AED 735
AED 2,018 total
includes taxes & fees
26 May - 27 May
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Exterior

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Onset
9.8 out of 10, Exceptional, (28 reviews)
"This place is beautiful, so clean and close to great restaurants and a clean and beautiful beach. We went to celebrate a birthday and it was perfect! "
United States
Larisa
The price is AED 823
AED 1,798 total
includes taxes & fees
26 May - 27 May
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
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.
View all properties

Top Osterville Hotel Reviews

Cape Sands Inn

Cape Sands Inn

6/10 Okay
"Shower in room was not maintained more water was coming out of the faucet than the shower head. Window in the room was not secure or locked and had no screens. This is a safety concern as kids could open it and fall out. Also the door to the room you could see daylight at the bottom bugs etc could crawl in. we put a towel on the floor to block it."
Emily 1-night trip
Posted 10 hours ago
Cape Sands Inn

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Osterville?
If you and your partner need a romantic escape, we've got just the ticket. If you want to explore the area, you might head to Cape Cod Beaches, Stand Up & Paddle Cape Cod, or Dowses Beach. If you're interested in staying near a certain attraction, 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 Osterville?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Osterville: 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 37°F. Average annual precipitation for Osterville is 52 inches.
What is there to do in Osterville?
There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all that Osterville has to offer. You might consider a visit to Cape Cod Beaches, Stand Up & Paddle Cape Cod, or Dowses Beach.
What's the best way to get to Osterville and around town during my romantic getaway?
This information about transportation options in Osterville might help your romantic trip get off to a smooth start: To get to Osterville, book a flight to Hyannis, MA (HYA-Barnstable Municipal), which is the closest major airport, located 5.8 mi (9.4 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.