Search Guest Houses in Osterville

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Compare 18 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, (42)
"Great lication and amneties"
The price is AED 349
AED 534 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
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 364
AED 909 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
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, (4)
"Everything was perfect"
The price is AED 123
AED 1,779 total
includes taxes & fees
7 Nov 2024 - 8 Nov 2024
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!!
7.8 out of 10, Good, (7)
"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
5 Nov 2024 - 6 Nov 2024
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
Mid Island Family retreat
First floor queen
Mid Island Family retreat
9.4 out of 10, Exceptional, (3)
"This was perfect for our annual trip - different as we usually stay 2 weeks and drive - but only 1 week this year and we flew in. The home was super cute and cozy. My daughter loved the loft! Would definitely recommend. Owners were super nice -allowed early entry for my friend until we arrived from Boston AND especially kind when our Uber Eats was left on their porch in the rain! Only issue were the little bugs/ants from outside coming inside. But hey that’s nature! Thanks for making our...
Mid Island Family retreat
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
9.6 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.
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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
9.2 out of 10, Wonderful, (36)
"Highly recommend."
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Edgewater Beach Resort, a VRI resort
Courtyard
Edgewater Beach Resort, a VRI resort
3.5 star property
8.8 out of 10, Excellent, (252)
"We loved our stay! The 1 bedroom was very clean fully equipped with everything we needed. All the extras like soap for dishes , dishwasher towels for the pool. Pool area very clean beautiful grounds. Friendly staff. "
Edgewater Beach Resort, a VRI resort
Oceanside 2 - SD335
Exterior
Oceanside 2 - SD335
9.8 out of 10, Exceptional, (12)
"House is set behind a dune. dune is a little steep, especially climbing back up. Kind of tough for the elderly. Set up of the house was good for 2 seniors. Many restaurants close by. Quiet area."
Oceanside 2 - SD335
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.