Search Guest Houses in Osterville

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Guest Houses in Osterville

Sea Breeze Inn
Exterior

Sea Breeze Inn

2.5 star property
8.0 out of 10, Very good, (173)
"Nice place to stay "
Sea Breeze Inn
The Lightkeepers Inn
Exterior

The Lightkeepers Inn

3.0 star property
9.6 out of 10, Exceptional, (183)
"Walking distance to coffee shops, restaurants, lighthouse beach; we were very happy with our stay. Look forward to visiting again next year. "
The Lightkeepers Inn
By the Sea Guests Bed & Breakfast & Suites
Outdoor wedding area

By the Sea Guests Bed & Breakfast & Suites

3.5 star property
9.4 out of 10, Exceptional, (173)
"Very nice property that sits on the beach. Friendly and helpful staff. Good breakfasts each day."
The price is NZ$527
includes taxes & fees
10 Aug - 11 Aug
By the Sea Guests Bed & Breakfast & Suites
All Seasons Resort
Indoor pool, outdoor pool

All Seasons Resort

9.0 out of 10, Wonderful, (50)
"Perfect!!!!"
The price is NZ$396
includes taxes & fees
28 July - 29 July
All Seasons Resort
Winstead Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

Winstead Inn

4.0 star property
9.4 out of 10, Exceptional, (117)
"The room was spacious and the shower was amazing!"
The price is NZ$680
includes taxes & fees
27 July - 28 July
Winstead Inn
Bright & Cozy with Patio, Grill and near the Beach & Golf
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"We needed a place to stay for a few days while visiting with family nearby. This "in-law apartment" was absolutely perfect for us in every way. Communications were great, info provided was 100% accurate, and we loved having our little private getaway. Will definitely stay again!!"
The price is NZ$742
includes taxes & fees
16 Aug - 17 Aug
Bright & Cozy with Patio, Grill and near the Beach & Golf
Fleetwing Guest House
House, 3 Bedrooms, Non Smoking | Terrace/patio

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
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, (8)
"thanks u for very nice place and clean i really loved i will cominng back soon"
The price is NZ$770
includes taxes & fees
27 July - 28 July
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Newly furnished-Enjoy sun drenched days w/ gentle breezes & fragrant salt air
Outdoor dining

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

2.0 star property
9.4 out of 10, Exceptional, (10)
"We had a great stay! House is in a nice location close to the beach, shops, and restaurants. The house is older but everything inside was brand new. It’s far enough from the main house that you don’t feel you are staying in someone’s guest house. Would definitely return!"
Newly furnished-Enjoy sun drenched days w/ gentle breezes & fragrant salt air
Spacious Guest House in Falmouth Village
1 bedroom, desk, iron/ironing board, travel cot

Spacious Guest House in Falmouth Village

8.6 out of 10, Excellent, (7)
"Great location Nice and clean Great people to work with"
The price is NZ$845
includes taxes & fees
10 Aug - 11 Aug
Spacious Guest House in Falmouth Village
Charming guest house set on horse farm, walk to downtown Edgartown
Dining

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

10.0 out of 10, Exceptional, (18)
"Great place with a wonderful owner. We hope to be back!"
Charming guest house set on horse farm, walk to downtown Edgartown
Woods Hole Passage Inn
Property grounds

Woods Hole Passage Inn

3.0 star property
9.6 out of 10, Exceptional, (59)
"Incredibly friendly hosts and excellent breakfast! "
Woods Hole Passage Inn
Beach family gateway, modern 5BR, walk to the beach, big yard, firepit
Sun-loungers, beach towels

Beach family gateway, modern 5BR, walk to the beach, big yard, firepit

10.0 out of 10, Exceptional, (12)
"Thoroughly enjoyed our stay. The house is spacious, yet warm and cozy. Very clean and convenient to the beach and town. Tanya is terrific, would definitely stay here again!"
Beach family gateway, modern 5BR, walk to the beach, big yard, firepit
The Oak Bluffs Inn
Deluxe Room, 2 Bedrooms

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
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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Top Osterville Hotel Reviews

Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"My husband and i had a wonderful wedding anniversary weekend. "
Andrea 2-night trip
Posted 15 hours ago
Hyannis Harbor Hotel