Cottage
10.0(92 Reviews)
2 Bedrooms
5 Guests
Parking
Ocean View
Balcony/Terrace
View
US $337/Night
7 Nights - US $2,356
Westerly Holiday Rentals
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Compare Villas, Resorts, & Rentals in Westerly
10.0
Bed & Breakfast
10.0(8 Reviews)
10 Bedrooms
20 Guests
Breakfast- Parking
- Balcony/Terrace
- View
US $413/Night
7 Nights - US $2,891
Bed & Breakfast
9.8(35 Reviews)
1 Bedroom
- Breakfast
- Parking
Internet
Sports/Activities
US $339/Night
7 Nights - US $2,375
Cottage
10.0(56 Reviews)
2 Bedrooms
7 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $1,684/Night
7 Nights - US $11,790
US $115/Night
7 Nights - US $803
House
10.0(55 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $475/Night
7 Nights - US $3,328
Apartment
10.0(36 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $273/Night
7 Nights - US $1,908
House
10.0(35 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $717/Night
7 Nights - US $5,019
Cottage
10.0(29 Reviews)
2 Bedrooms
6 Guests
Private Pool- Oceanfront
- Parking
Pool
US $868/Night
7 Nights - US $6,075
Luxury Holiday Rentals in Westerly
Over 308+ Luxury Holiday Rentals in or Near Westerly
Villa
7 Bedrooms
14 Guests
- Oceanfront
Hot Tub- Parking
- Pool
US $6,125/Night
7 Nights - US $42,872
House
10.0(21 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $3,052/Night
7 Nights - US $21,362
House
5 Bedrooms
10 Guests
Air Conditioner- Internet
Child Friendly
Laundry
US $2,269/Night
7 Nights - US $15,886
Condo
10.0(9 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $2,221/Night
7 Nights - US $15,547
Cottage
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $2,099/Night
7 Nights - US $14,695
House
4 Bedrooms
8 Guests
- Parking
- Ocean View
- View
Kitchen
US $1,935/Night
7 Nights - US $13,544
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,738/Night
7 Nights - US $12,168
House
10.0(74 Reviews)
6 Bedrooms
17 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,725/Night
7 Nights - US $12,074
Condo
10.0(25 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,693/Night
7 Nights - US $11,848
Top-Rated Holiday Rentals with a Pool in Westerly
Over 31+ The Best Private Villas and Holiday Rentals in Westerly with a Pool
House
10.0(44 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $799/Night
7 Nights - US $5,590
House
10.0(23 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $617/Night
7 Nights - US $4,321
House
10.0(15 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,133/Night
7 Nights - US $7,928
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $789/Night
7 Nights - US $5,524
Bed & Breakfast
9.9(23 Reviews)
8 Bedrooms
32 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
US $401/Night
7 Nights - US $2,804
House
9.8(30 Reviews)
5 Bedrooms
13 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,293/Night
7 Nights - US $9,049
House
9.8(19 Reviews)
3 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,172/Night
7 Nights - US $8,203
House
9.8(12 Reviews)
6 Bedrooms
11 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,515/Night
7 Nights - US $10,606
US $207/Night
7 Nights - US $1,450
Pet-Friendly Holiday Rentals in Westerly
Over 59+ Pet-Friendly Holiday Rentals in or Near Westerly
House
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $484/Night
7 Nights - US $3,386
House
3 Bedrooms
7 Guests
- Internet
Pet Friendly- Child Friendly
Security/Safety
US $1,214/Night
7 Nights - US $8,495
Condo
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $1,577/Night
7 Nights - US $11,036
US $134/Night
7 Nights - US $940
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $383/Night
7 Nights - US $2,681
Cottage
9.8(175 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $211/Night
7 Nights - US $1,480
Cottage
9.8(70 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $249/Night
7 Nights - US $1,745
Cottage
9.6(56 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $291/Night
7 Nights - US $2,040
Cottage
9.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $388/Night
7 Nights - US $2,713
Large Holiday Rentals and Private Villas in Westerly
Over 61+ Large Holiday Rentals and Private Villas in or Near Westerly
House
10.0(62 Reviews)
5 Bedrooms
14 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,014/Night
7 Nights - US $7,095
Bed & Breakfast
9.6(26 Reviews)
7 Bedrooms
15 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
US $436/Night
7 Nights - US $3,051
House
10.0(51 Reviews)
5 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,346/Night
7 Nights - US $9,419
Bed & Breakfast
7.3(6 Reviews)
7 Bedrooms
15 Guests
- Parking
- Air Conditioner
- Internet
US $195/Night
7 Nights - US $1,365
House
10.0(35 Reviews)
4 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,575/Night
7 Nights - US $11,028
House
10.0(31 Reviews)
6 Bedrooms
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,662/Night
7 Nights - US $11,633
House
10.0(20 Reviews)
3 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $678/Night
7 Nights - US $4,744
Villa
10.0(15 Reviews)
6 Bedrooms
16 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,519/Night
7 Nights - US $10,632
House
10.0(3 Reviews)
5 Bedrooms
14 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $1,635/Night
7 Nights - US $11,446
Wheelchair Accessible Holiday Homes in Westerly
Over 8+ Wheelchair Accessible Holiday Homes in or Near Westerly
Condo
10.0(56 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,172/Night
7 Nights - US $8,207
US $382/Night
7 Nights - US $2,671
US $243/Night
7 Nights - US $1,701
US $293/Night
7 Nights - US $2,049
US $683/Night
7 Nights - US $4,780
US $1,200/Night
7 Nights - US $8,400
US $167/Night
7 Nights - US $1,166
US $161/Night
7 Nights - US $1,128
Westerly Private Villas and Holiday Homes Under $200
Over 29+ Westerly Private Villas and Holiday Homes Under $200
Condo
10.0(1 Review)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $76/Night
7 Nights - US $533
House
8.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Internet
- Child Friendly
- Security/Safety
US $135/Night
7 Nights - US $945
US $182/Night
7 Nights - US $1,271
Apartment
9.2(18 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $182/Night
7 Nights - US $1,277
US $184/Night
7 Nights - US $1,289
House
10.0(18 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $172/Night
7 Nights - US $1,204
Apartment
10.0(33 Reviews)
2 Bedrooms
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $160/Night
7 Nights - US $1,118
House
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $103/Night
7 Nights - US $723
House
10.0(4 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $177/Night
7 Nights - US $1,239
Instantly Bookable Holiday Homes in Westerly
Over 111+ Instantly Bookable Holiday Homes in or Near Westerly
House
10.0(22 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $397/Night
7 Nights - US $2,781
House
10.0(8 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $357/Night
7 Nights - US $2,500
Cottage
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $547/Night
7 Nights - US $3,830
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,598/Night
7 Nights - US $11,185
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $556/Night
7 Nights - US $3,892
Cottage
9.8(94 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $322/Night
7 Nights - US $2,254
Condo
9.4(3 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $982/Night
7 Nights - US $6,875
Apartment
9.0(2 Reviews)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $278/Night
7 Nights - US $1,945
Apartment
6.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $257/Night
7 Nights - US $1,799
Book a Last Minute Place to Stay in Westerly
About Casai's Private Villas and Holiday Rentals in Westerly
Discover more than 317 vacation rentals available in Westerly. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Westerly.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Westerly, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Westerly. On average, places to stay near Westerly offer 735.14 ft², with nightly prices averaging US $714.
With Casai, finding and comparing holiday rentals in Westerly is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Westerly, RI
There are 317 Westerly, RI Holiday Rentals
- Prices for a holiday home in Westerly start at US $76
- Top rated vacation home in Westerly is Amazing Ocean Front 2 Story Home, Steps Away From The Water
- Most popular short term in Westerly is Winnapaug Inn
- Cheapest place to stay in Westerly is Loft-style guest house in the heart of Westerly! All new everything, sleeps 4
- Most expensive holiday rental in Westerly is Luxurious expansive villa in prestigious Watch Hill set on 5 acres
Recently Booked Holiday Rentals in Westerly
Frequently Asked Questions About Westerly?
What are the top holiday rentals in Westerly?
With numerous options available in Westerly, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Westerly:
- Amazing Ocean Front 2 Story Home, Steps Away From The Water
- Relaxing Getaway with Town Beach Access
- Classic Cozy Cottage in Watch Hill
- Summer Wind Beach House!
- Family Friendly Beach Gathering Place
- Ocean Front Cottage With Private Beach On Watch Hill End of Westerly
- Available for Fall Winter and Spring monthly rental, incredible Ocean View. .
- Custom cottage close to everything-Enjoy long walks on beach without the crowds!
- "The Boulders" - A Watch Hill Five Bedroom House
- Beautiful Large Home in Westerly walking distance to downtown !
How many holiday rentals have private pools in Westerly?
Discover a selection of holiday rentals with private pools near Westerly with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Westerly are best for families?
If you're searching for a family-friendly holiday home in Westerly, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Westerly:
How many Casai.com holiday rentals are available in Westerly?
As of 2026, Casai boasts over 317 properties listed in the Westerly area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Westerly.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Watch Hill Historic District Vacation Rentals in Westerly, Rhode Island | 199 |
