Title: Osterville Guest Houses from CA $200 | Expedia.ca

  

[Osterville Travel Guide](https://expedia.ca/Osterville.dx183338)[Hotels in Osterville](https://expedia.ca/Osterville-Hotels.d183338.Travel-Guide-Hotels)[Vacation Rentals in Osterville](https://expedia.ca/Osterville-Vacation-Rentals.d183338.Travel-Guide-VacationRentals)[Osterville Car Rentals](https://expedia.ca/Car-Rentals-In-Osterville.d183338.Car-Rental-Guide)[Osterville Vacation Packages](https://expedia.ca/Osterville.d183338.Destination-Travel-Guides)

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# Search Guest Houses in Osterville from CA $200

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## Check prices for these dates

Next weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183338&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Osterville Guest Houses

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/cb9a8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/29e47360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/f546da25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/7000000/6170000/6165700/6165614/0959237c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winstead Inn

Harwich

9.4/10

Exceptional

(125)

"Windstead Inn is a beautiful property!! Management was great, let us check in early and our room was upgraded. Would definitely stay again."

CA $235

CA $285 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Harwich-Hotels-Winstead-Inn.h6165614.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1560000/1556000/1555968/719ceca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Room | Bathroom](https://images.trvl-media.com/lodging/2000000/1560000/1556000/1555968/79297ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Cottage, Multiple Bedrooms | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1560000/1556000/1555968/f3e77f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1560000/1556000/1555968/f458ac0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sea Breeze Inn

Hyannis

7.8/10

Good

(192)

"Property was very conveniently located. Management was very easy to contact and very responsive. We needed a place to stay for a wedding and this was the right price, A/C worked great and quiet."

CA $175

CA $200 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Hyannis-Hotels-Sea-Breeze-Inn.h1555968.Hotel-Information)

![Outdoor wedding area](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/5982af75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private Yellowtail House at By the Sea Bed & Breakfast | Private kitchen](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/31b48c81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private Yellowtail House at By the Sea Bed & Breakfast | Private kitchen](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/0ae72b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, 1 Queen Bed with Sofa bed, Private Bathroom, Partial Ocean View (1 Bdrm. Suite) | View from room](https://images.trvl-media.com/lodging/10000000/9810000/9801600/9801551/5576d037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### By the Sea Guests Bed & Breakfast & Suites

Dennis Port

9.2/10

Wonderful

(184)

"Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!"

CA $259

CA $337 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Dennis-Port-Hotels-By-The-Sea-Guests-Bed-Breakfast-Suites.h9801551.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/d11aa513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 Queen Bed with Sofa bed | Living area](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/27eb2c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 1 King Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/430aaed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11180000/11172600/11172592/d6b2594e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lightkeepers Inn

Edgartown

9.4/10

Exceptional

(201)

"Location and neighborhood were quiet residential area outside of main tourist street. "

CA $261

CA $291 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Edgartown-Hotels-The-Lightkeepers-Inn.h11172592.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/w2388h1514x0y77-1097f3b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/a1cc2110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/0fb3af2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/55000000/54940000/54935300/54935241/b25bc447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

CA $3,502

CA $5,452 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Oak-Bluffs-Hotels-Beautiful-Estate-With-Salt-Water-Pool-Pond-With-Kayaks.h54935241.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28&regionId=183338&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true)

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## Top Osterville Hotel Reviews

![Cape Sands Inn](//images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682_y.jpg)

### Cape Sands Inn

10/10 Excellent

"OK"

[](https://expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.Hotel-Information)

![Hyannis Travel Inn](//images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg)

### Hyannis Travel Inn

10/10 Excellent

"The staff is very friendly and helpful. Highly recommended!"

[](https://expedia.ca/Hyannis-Hotels-Hyannis-Travel-Inn.h1379109.Hotel-Information)

![Sunbird Cape Cod Resort](//images.trvl-media.com/lodging/80000000/79410000/79402900/79402816/e6eb20e4_y.jpg)

### Sunbird Cape Cod Resort

10/10 Excellent

"We enjoyed peace and quiet, the room was huge, very clean, and with all amenities. The breakfast had hot items like sausage and scrambled eggs, and decaf coffee. Internet and TV were working great. The staff was beyond wonderful."

[](https://expedia.ca/West-Yarmouth-Hotels-Sunbird-Cape-Cod-Resort.h79402816.Hotel-Information)

![Faraway Martha's Vineyard](//images.trvl-media.com/lodging/1000000/70000/65700/65623/10e4fb42_y.jpg)

### Faraway Martha's Vineyard

10/10 Excellent

"Quick overnight, nice facility room better than adequate."

[](https://expedia.ca/Edgartown-Hotels-Faraway-Marthas-Vineyard.h65623.Hotel-Information)

![Hampton Inn & Suites Cape Cod-West Yarmouth](//images.trvl-media.com/lodging/3000000/2560000/2558700/2558618/dc2c7156_y.jpg)

### Hampton Inn & Suites Cape Cod-West Yarmouth

10/10 Excellent

"Nice place. Clean and comfy bed. "

[](https://expedia.ca/West-Yarmouth-Hotels-Hampton-Inn-Suites-Cape-Cod-West-Yarmouth.h2558618.Hotel-Information)

![Summercamp](//images.trvl-media.com/lodging/11000000/10060000/10058600/10058501/4ff1c19a_y.jpg)

### Summercamp

10/10 Excellent

"Awesome"

[](https://expedia.ca/Oak-Bluffs-Hotels-Summercamp.h10058501.Hotel-Information)

![Iris Hotel Cape Cod ](//images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190_y.jpg)

### Iris Hotel Cape Cod

10/10 Excellent

"Clean room, friendly staff"

[](https://expedia.ca/Falmouth-Hotels-Hotel-Cape-Cod.h11989.Hotel-Information)

![Hyannis Harbor Hotel](//images.trvl-media.com/lodging/1000000/60000/55000/54945/741b5772_y.jpg)

### Hyannis Harbor Hotel

10/10 Excellent

"Execelwl "

[](https://expedia.ca/Hyannis-Hotels-Hyannis-Harbor-Hotel.h54945.Hotel-Information)

![Bayside Resort Hotel](//images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg)

### Bayside Resort Hotel

10/10 Excellent

"Fantastic time"

[](https://expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information)

## Find out more about Osterville

## Osterville Guest Houses information

| Number of reviews | 701 |
| --- | --- |
| Accommodation | 14 Guest Houses |
| Lowest Price | CA $200 |
| Highest Price | CA $337 |

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-   [Villas in Sandalwood Village](https://www.expedia.ca/Sandalwood-Village-Villas.d553248635976384160-aaVillas.Travel-Guide-Accommodation)
-   [Hotels near Veterans Memorial Park](https://www.expedia.ca/Veterans-Memorial-Park-Hotels.0-l553248621532666520-0.Travel-Guide-Filter-Hotels)
-   [B&B in West Barnstable](https://www.expedia.ca/West-Barnstable-Bed-And-Breakfast.d183348-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Beach Hotel Hotels in West Barnstable](https://www.expedia.ca/West-Barnstable-Hotels-Beach-Hotel.0-0-d183348-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in West Barnstable](https://www.expedia.ca/West-Barnstable-Hotels-Luxury-Hotel.0-0-d183348-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in West Barnstable](https://www.expedia.ca/West-Barnstable-Hotels-Spa-Hotel.0-0-d183348-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [West Barnstable Hotels](https://www.expedia.ca/West-Barnstable-Hotels.d183348.Travel-Guide-Hotels)
-   [Townhomes in West Barnstable](https://www.expedia.ca/West-Barnstable-Townhomes.d183348-aaTownhomes.Travel-Guide-Accommodation)
-   [Cabin Rentals in West Hyannisport](https://www.expedia.ca/West-Hyannisport-Cabins.d6285896-aaCabins.Travel-Guide-Accommodation)

-   [Flights to Hyannis](https://www.expedia.ca/Cheap-Flights-To-Hyannis.d1544.Travel-Guide-Flights)
-   [Flights from Mashpee](https://www.expedia.ca/lp/flights/130591/flights-from-mashpee)

-   [Cape Codder Water Park](https://www.expedia.ca/Cape-Codder-Water-Park-Hyannis.d553248635056398978.Vacation-Attraction)
-   [Visit Centerville](https://www.expedia.ca/Centerville.dx88031)
-   [Cotuit Center for the Arts](https://www.expedia.ca/Cotuit-Center-For-The-Arts-Cotuit.d553248621532666433.Vacation-Attraction)
-   [Craigville Beach](https://www.expedia.ca/Craigville-Beach-Centerville.d6287483.Vacation-Attraction)
-   [Hyannis Port Vacations](https://www.expedia.ca/Hyannis-Port.d183332.Destination-Travel-Guides)
-   [Visit Hyannis Port](https://www.expedia.ca/Hyannis-Port.dx183332)
-   [Visit Hyannis](https://www.expedia.ca/Hyannis.dx1544)
-   [John F. Kennedy Hyannis Museum](https://www.expedia.ca/John-F-Kennedy-Hyannis-Museum-Hyannis.d6070185.Vacation-Attraction)
-   [John F. Kennedy Memorial](https://www.expedia.ca/John-F-Kennedy-Memorial-Hyannis.d6286978.Vacation-Attraction)
-   [Keyes Beach](https://www.expedia.ca/Keyes-Beach-Hyannis.d553248635983989303.Vacation-Attraction)
-   [Visit Popponesset Island](https://www.expedia.ca/Popponesset-Island.dx553248635976384780)
-   [Visit West Hyannisport](https://www.expedia.ca/West-Hyannisport.dx6285896)

-   [Car rental Hyannis Port](https://www.expedia.ca/Car-Rentals-In-Hyannis-Port.d183332.Car-Rental-Guide)
-   [Rent A Wreck Rental Cars in Hyannis](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Hyannis.d1544-c33.Car-Rental-Guide-Suppliers)

-   [Hyannis Port Vacation Rentals](https://www.expedia.ca/Hyannis-Port-Vacation-Rentals.d183332.Travel-Guide-VacationRentals)
-   [Hyannis Vacation Rentals](https://www.expedia.ca/Hyannis-Vacation-Rentals.d1544.Travel-Guide-VacationRentals)

-   [Things to do in Hyannis](https://www.expedia.ca/Things-To-Do-In-Hyannis.d1544.Travel-Guide-Activities)
-   [Things to do in Marstons Mills](https://www.expedia.ca/Things-To-Do-In-Marstons-Mills.d6285640.Travel-Guide-Activities)
-   [Things to do in Mashpee](https://www.expedia.ca/Things-To-Do-In-Mashpee.d130591.Travel-Guide-Activities)
-   [Things to do in Popponesset Island](https://www.expedia.ca/Things-To-Do-In-Popponesset-Island.d553248635976384780.Travel-Guide-Activities)

-   [Book Guest Houses in Osterville on Expedia.com](https://www.expedia.com/Osterville-Guest-Houses.d183338-aaGuestHouses.Travel-Guide-Accommodation)