Search Guest Houses in Osterville

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 19 Guest Houses in Osterville with updated reviews, rates, and availability.

Winstead Inn
Front of property - evening/night

Winstead Inn

4.0 star property
9.4 out of 10, Exceptional, (111)
"Staff was great. "
Winstead Inn
Sea Breeze Inn
Exterior

Sea Breeze Inn

2.5 star property
8.0 out of 10, Very Good, (147)
"This was just what we needed, no frills clean Bed and Shower, Walk to beach !"
Sea Breeze Inn
All Seasons Resort
Exterior

All Seasons Resort

9.2 out of 10, Wonderful, (43)
"We were very comfortable. Tiffany and Trudy were very friendly, knowledgeable and spot-on with their recommendations!"
The price is AED 349
AED 534 total
includes taxes & fees
24 Nov - 25 Nov
All Seasons Resort
By the Sea Guests Bed & Breakfast & Suites
Beach

By the Sea Guests Bed & Breakfast & Suites

3.5 star property
9.4 out of 10, Exceptional, (162)
"Tom was very nice an upgraded us to a suite. The breakfast was exceptional. The persons serving were very pleasant."
By the Sea Guests Bed & Breakfast & Suites
Spacious Guest House in Falmouth Village
Guest House entrance and comfy Adirondack chairs for your enjoyment

Spacious Guest House in Falmouth Village

8.0 out of 10, Very Good, (2)
"Excellent location, private. Very clean. 5 *"
Spacious Guest House in Falmouth Village
Woods Hole Passage Inn
Front of property

Woods Hole Passage Inn

3.0 star property
9.6 out of 10, Exceptional, (59)
"The property was wonderful and the host was excellent. I had lots of questions during our stay as it was our first time in Falmouth, and the host made sure we had answers to everything we needed. They even had a binder full of local recommendations in the room when we checked in! "
Woods Hole Passage Inn
Newly furnished-Enjoy sun drenched days w/ gentle breezes & fragrant salt air

Newly furnished-Enjoy sun drenched days w/ gentle breezes & fragrant salt air

2.0 star property
9.4 out of 10, Exceptional, (6)
"Ok"
Newly furnished-Enjoy sun drenched days w/ gentle breezes & fragrant salt air
Bright & Cozy with Patio, Grill and near the Beach & Golf
Primary bedroom with a comfortable queen bed and plenty of space to store your clothes.

Bright & Cozy with Patio, Grill and near the Beach & Golf

2.0 star property
10.0 out of 10, Exceptional, (5)
"This was a perfect respite after following our kid around the golf course!!"
The price is AED 327
AED 865 total
includes taxes & fees
25 Nov - 26 Nov
Bright & Cozy with Patio, Grill and near the Beach & Golf
Fleetwing Guest House
Exterior

Fleetwing Guest House

2.0 star property
10.0 out of 10, Exceptional, (1)
"Had a wonderful stay at the fleetwing guest house. Beautiful restoration of an 1800' s stable house, still has original flooring. Very clean, nice beds, big upstairs room for families. Easy bike ride to beach or downtown shops and restaurants, and had a nice night sitting by the fire pit in a private back yard. Property owner was very prompt and helpful with any questions, will definitely be back!"
Fleetwing Guest House
"Awesome Vacation while staying at "HomeAway" from Home"

"Awesome Vacation while staying at "HomeAway" from Home"

8.4 out of 10, Very Good, (71)
"Loved out stay. Great place. Definitely stay again"
"Awesome Vacation while staying at "HomeAway" from Home"
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Exterior

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3.0 star property
10.0 out of 10, Exceptional, (5)
"Everything was perfect"
The price is AED 123
AED 1,779 total
includes taxes & fees
5 Dec - 6 Dec
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
The Lightkeepers Inn
Exterior

The Lightkeepers Inn

3.0 star property
9.6 out of 10, Exceptional, (174)
"A lovely spot near the downtown, shopping, restaurants and the wharf. It had everything we needed."
The Lightkeepers Inn
The Mariner Resort on Cape Cod!!
Room

The Mariner Resort on Cape Cod!!

8.0 out of 10, Very Good, (8)
"Everything was dirty. The room was dirty. The bathroom was dirty. The pool was dirty. The hot tub was dirty. Even the golf course was covered with debris so that you couldn’t play. It was completely rundown. I would never stay there again."
The price is AED 367
AED 631 total
includes taxes & fees
24 Nov - 25 Nov
The Mariner Resort on Cape Cod!!
Charming guest house set on horse farm, walk to downtown Edgartown
Private kitchen

Charming guest house set on horse farm, walk to downtown Edgartown

10.0 out of 10, Exceptional, (16)
"We enjoyed our stay at the guest house. The location is lovely on a quiet horse farm with easy access to the nearby bike path and road into town. The guest house is attached to the main house but with a private and respectful feel. The house is well stocked and the kitchen is top grade. The bedrooms upstairs are small but comfortable. Would return. "
Charming guest house set on horse farm, walk to downtown Edgartown
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds
Exterior

,Artist Guest House on beautiful estate open concept King Sized Bunk Beds

10.0 out of 10, Exceptional, (2)
"Cozy and peaceful place to stay for my sister and me. Had everything we needed. Close to bus routes. Would definitely go back!"
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds
Inn on the Beach
Exterior

Inn on the Beach

3.0 star property
9.2 out of 10, Wonderful, (25)
"The staff was great but the room wasn’t what we thought it would be. We thought it would be small house/condos but it’s set up more like a motel type style. The bed is EXTREMELY firm"
Inn on the Beach
The Oak Bluffs Inn
Front of property

The Oak Bluffs Inn

3.0 star property
9.6 out of 10, Exceptional, (11)
"Such a beautiful, unique spot. Great location, I'll definitely be back."
The Oak Bluffs Inn
Madison Inn
Front of property

Madison Inn

2.5 star property
9.8 out of 10, Exceptional, (76)
"Great location! Very clean rooms and friendly staff."
Madison Inn
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.
Don't see what you're looking for?
See all available properties in Osterville
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Osterville

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower

9.4 out of 10, Exceptional, (38)
"We enjoyed the time spending there. That is mostly fit us well due to the circumstance for which we were there. My wife liked every minute of it and so did I; but I simply wish there were some coffee there, along with the coffee maker. So, I wouldn’t have to go out just for that, the first night we got there. "
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
The Club at New Seabury
Outdoor pool

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (304)
"will definitely go back again .. awesome place! "
The price is AED 542
AED 620 total
includes taxes & fees
24 Nov - 25 Nov
The Club at New Seabury
Edgewater Beach Resort, a VRI resort
Courtyard

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (254)
"This was my second stay here and it was lovely. We visited in November for a mother/daughters trip and stayed in the two bedroom suite. Rooms were very clean, had plenty of extra towels and the fireplace was lovely. We used the pool as well and walked on the beach. At sunrise on the beach we had a seal swim up and say hello. Excellent place to have a little R&R"
Edgewater Beach Resort, a VRI resort
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.