Estia Villas - Vacation Rentals in Osterville
House
10.0
(
89 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
3300 ft²
-
Oceanfront -
Parking -
Ocean View -
Balcony/Terrace
US $1,181
/Night
7 Nights - $8,268
House
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
505.9 ft²
-
Parking
-
Balcony/Terrace
-
Internet -
Child Friendly
US $390
/Night
7 Nights - $2,730
House
9.8
(
45 Reviews
)
4 Bedrooms
3 Bathrooms
11 Guests
3700 ft²
-
Private Pool -
Oceanfront
-
Parking
-
Pool
US $2,284
/Night
7 Nights - $15,987
House
9.4
(
18 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
2400 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $780
/Night
7 Nights - $5,460
House
10.0
(
25 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2700 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $511
/Night
7 Nights - $3,578
House
10.0
(
18 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $909
/Night
7 Nights - $6,361
House
10.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $406
/Night
7 Nights - $2,840
House
10.0
(
3 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $956
/Night
7 Nights - $6,695
See More Osterville Vacation Rentals
Luxury Places to Stay in Osterville
Over 157+
Luxury Places to Stay in or Near Osterville
House
6 Bedrooms
7 Bathrooms
22 Guests
-
Private Pool
-
Oceanfront
-
Hot Tub -
Parking
US $6,142
/Night
7 Nights - $42,994
House
10.0
(
2 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $5,605
/Night
7 Nights - $39,237
House
10.0
(
1 Review
)
6 Bedrooms
5 Bathrooms
12 Guests
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $5,055
/Night
7 Nights - $35,383
House
10.0
(
3 Reviews
)
4 Bedrooms
5 Bathrooms
10 Guests
-
Private Pool
-
Hot Tub
-
Pool
-
Air Conditioner
US $5,017
/Night
7 Nights - $35,119
House
9.2
(
9 Reviews
)
11 Bedrooms
7 Bathrooms
22 Guests
7400 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $4,048
/Night
7 Nights - $28,339
House
5 Bedrooms
6 Bathrooms
18 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $3,052
/Night
7 Nights - $21,364
House
Waterfront Estate in Prestigious Osterville | Private Beach, Pool & Hot Tub and Central AC-Sleeps 15
9.6
(
5 Reviews
)
6 Bedrooms
5 Bathrooms
15 Guests
4470 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $3,009
/Night
7 Nights - $21,064
House
6 Bedrooms
7 Bathrooms
12 Guests
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $2,730
/Night
7 Nights - $19,108
See More Osterville Luxury Vacation Rentals
Find More Osterville Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Osterville
Over 35+
Top-Rated Vacation Rentals with a Pool in or Near Osterville
House
9.8
(
35 Reviews
)
7 Bedrooms
7 Bathrooms
10 Guests
7000 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $1,729
/Night
7 Nights - $12,105
House
9.6
(
4 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1344 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $519
/Night
7 Nights - $3,636
House
9.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
10 Guests
1926.74 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $824
/Night
7 Nights - $5,768
House
8.4
(
5 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1930 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $520
/Night
7 Nights - $3,639
House
8.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
8 Guests
1345.49 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
View
US $420
/Night
7 Nights - $2,940
House
5 Bedrooms
4 Bathrooms
10 Guests
3800 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $1,688
/Night
7 Nights - $11,814
House
4 Bedrooms
2 Bathrooms
8 Guests
3387 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $590
/Night
7 Nights - $4,130
House
4 Bedrooms
2 Bathrooms
8 Guests
1926.74 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
View
US $571
/Night
7 Nights - $3,996
Pet-Friendly Vacation Rentals in Osterville
Over 44+
Pet-Friendly Vacation Rentals in or Near Osterville
House
10.0
(
2 Reviews
)
4 Bedrooms
3 Bathrooms
6 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $742
/Night
7 Nights - $5,195
House
1 Bedroom
1 Bathroom
10 Guests
2454.17 ft²
-
Parking
-
View
-
Air Conditioner
-
Internet
US $1,112
/Night
7 Nights - $7,785
House
9.8
(
6 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2900 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,605
/Night
7 Nights - $11,235
House
5 Bedrooms
4 Bathrooms
10 Guests
2450 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,369
/Night
7 Nights - $9,586
House
3 Bedrooms
2 Bathrooms
6 Guests
1671 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $848
/Night
7 Nights - $5,933
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,521
/Night
7 Nights - $10,645
House
10.0
(
6 Reviews
)
8 Bedrooms
7 Bathrooms
20 Guests
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $2,316
/Night
7 Nights - $16,215
New
House
10.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
11 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,128
/Night
7 Nights - $7,897
See More Pet-Friendly Vacation Rentals in Osterville on PetFriendly.io
Large Vacation Homes & Villas in Osterville
Over 31+
Large Vacation Homes & Villas in or Near Osterville
House
9.6
(
4 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
2758 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,530
/Night
7 Nights - $10,711
House
5 Bedrooms
4 Bathrooms
10 Guests
-
Balcony/Terrace
-
View
-
Air Conditioner
-
Barbecue/Outdoor Cooking
US $1,366
/Night
7 Nights - $9,563
House
10.0
(
2 Reviews
)
6 Bedrooms
5 Bathrooms
15 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,363
/Night
7 Nights - $9,541
House
9.6
(
20 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $683
/Night
7 Nights - $4,778
House
8.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
10 Guests
3200 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $875
/Night
7 Nights - $6,124
House
5 Bedrooms
3 Bathrooms
10 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,987
/Night
7 Nights - $13,908
House
7 Bedrooms
4 Bathrooms
12 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,962
/Night
7 Nights - $13,737
House
4 Bedrooms
3 Bathrooms
10 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,475
/Night
7 Nights - $10,325
See More Family Vacation Rentals in Osterville on FVR
Wheelchair Accessible Vacation Homes in Osterville
Over 1+
Wheelchair Accessible Vacation Homes in or Near Osterville
House
5.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2400 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $450
/Night
7 Nights - $3,150
Osterville Vacation Rentals and Airbnb Places to Stay Under $200
Over 2+
Osterville Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
4 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
764 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $147
/Night
7 Nights - $1,029
Apartment
2 Bedrooms
1 Bathroom
4 Guests
796.53 ft²
-
Private Beach -
Oceanfront
-
Breakfast -
Parking
US $126
/Night
7 Nights - $882
See More Osterville Vacation Rental Deals
Instantly Bookable Vacation Homes in Osterville
Over 59+
Instantly Bookable Vacation Homes in or Near Osterville
House
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
500 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $468
/Night
7 Nights - $3,279
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
1600 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $642
/Night
7 Nights - $4,492
Cottage
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
3 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $539
/Night
7 Nights - $3,771
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
1288 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $482
/Night
7 Nights - $3,374
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Balcony/Terrace
-
Internet
-
Child Friendly
-
Laundry
US $456
/Night
7 Nights - $3,194
House
9.6
(
4 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
TV
US $472
/Night
7 Nights - $3,301
House
9.4
(
13 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1512 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $545
/Night
7 Nights - $3,813
Cottage
8.6
(
11 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $457
/Night
7 Nights - $3,202
About Osterville Vacation Rentals
With more than 166 Osterville vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Osterville.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Osterville, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Osterville. Places to stay near Osterville are 1080.52 ft² on average, with prices averaging US $1,175 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Osterville with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Osterville
| Type | Count |
|---|---|
| Vacation Homes | 157 |
| Cottages | 6 |
| Holiday Apartments | 2 |
Use these Quick Filters to Find a Vacation Rental in Osterville
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osterville.
Weather in Osterville
View the weather forecast for Osterville before booking your Osterville Vacation Rentals to confirm your best time to go.
December - February
High 45°F Low 24°F
March - May
High 66°F Low 27°F
June - August
High 81°F Low 59°F
September - November
High 77°F Low 35°F
Top Attractions Around Osterville, MA
Estiavillas offers a large selection of top attractions around Osterville. Research things to do on your vacation before you visit Osterville.
Stand Up & Paddle Cape Cod
Dowses Beach
Public Beach
Cape Codder Water Park
Harwich Port
Hyannis Harbor
Old Silver Beach
Mayflower Beach
Oak Bluffs Harbor
Inkwell Beach
West Dennis Beach
Seagull Beach
Sandy Neck Beach
Hyannis Port Beach
Falmouth Heights Beach
Katama Beach
Massachusetts Maritime Academy
Woods Hole Ferry Terminal
Water Wizz
Craigville Beach
Other Places to Stay Near Osterville, MA
Osterville Vacation Rental Frequently Asked Questions
How many vacation rentals have private pools in Osterville?
There are 22 vacation rentals with private pools near Osterville. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Osterville are best for families?
If you are looking for a family-friendly vacation home in Osterville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osterville:
How many vacation rentals are available in Osterville?
Currently, the total number of properties listed in 2026 is over 166 in the Osterville area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osterville.
