Cheapside, St. Michael Vacation Rentals & Ski-in/Ski-out Homes
Condo
- Christ Church
- ·
- Hastings
- 0.28 mi to center
10.0Exceptional
(44 Reviews)
2 Bedrooms
2 Baths
4 Guests
Oceanfront
Parking
Pool
Ocean View
US $387/Night
7 Nights - US $2,707
House
- Bridgetown
- ·
- Brighton
- 0.28 mi to center
10.0Exceptional
(3 Reviews)
8 Bedrooms
9 Baths
16 Guests
3751.22 ft²
- Oceanfront
Hot Tub- Parking
- Pool
US $1,300/Night
7 Nights - US $9,100
Apartment
10.0Exceptional
(21 Reviews)
1 Bedroom
1 Bath
6 Guests
Private Pool- Parking
- Pool
- Ocean View
US $136/Night
7 Nights - US $952
Apartment
- Bridgetown
- ·
- Black Rock
- 0.41 mi to center
10.0Exceptional
(29 Reviews)
1 Bedroom
2 Baths
2 Guests
264 ft²
- Parking
- Ocean View
Balcony/Terrace
View
US $76/Night
7 Nights - US $532
Apartment
10.0Exceptional
(3 Reviews)
8 Bedrooms
7 Baths
17 Guests
- Oceanfront
Breakfast- Parking
- Ocean View
US $312/Night
7 Nights - US $2,185
House
10.0Exceptional
(24 Reviews)
4 Bedrooms
5 Baths
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,725/Night
7 Nights - US $12,075
Cottage
- Rockley
- ·
- Marine Gardens
- 0.09 mi to center
10.0Exceptional
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $205/Night
7 Nights - US $1,432
Apartment
- Christ Church
- ·
- Hastings
- 0.12 mi to center
10.0Exceptional
(23 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $408/Night
7 Nights - US $2,857
Apartment
- Rockley
- ·
- Marine Gardens
- 0.10 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $212/Night
7 Nights - US $1,482
Luxury Places to Stay in Cheapside
Over 885+ Luxury Places to Stay in or Near Cheapside
House
- St. Michael
- ·
- Bridgetown
- 1.56 mi to center
8 Bedrooms
7 Baths
16 Guests
- Parking
- Pool
Kitchen
Internet
US $5,582/Night
7 Nights - US $39,076
House
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $4,225/Night
7 Nights - US $29,575
House
5 Bedrooms
5 Baths
10 Guests
Air Conditioner- Internet
Pet Friendly
Child Friendly
US $3,162/Night
7 Nights - US $22,136
House
- St. Michael
- ·
- Bridgetown
- 0.81 mi to center
9 Bedrooms
10 Baths
37 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $2,241/Night
7 Nights - US $15,687
US $2,089/Night
7 Nights - US $14,623
Villa
10.0Exceptional
(2 Reviews)
7 Bedrooms
5 Baths
12 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,610/Night
7 Nights - US $11,272
Apartment
- Bridgetown
- ·
- Spring Garden
- 0.25 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
4 Baths
6 Guests
3000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,534/Night
7 Nights - US $10,737
Condo
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
9.8Exceptional
(8 Reviews)
3 Bedrooms
3 Baths
6 Guests
1666 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,289/Night
7 Nights - US $9,025
Villa
3 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- View
US $1,225/Night
7 Nights - US $8,572
Top-Rated Vacation Rentals with a Pool in Cheapside
Over 350+ Top-Rated Vacation Rentals with a Pool in or Near Cheapside
Condo
- Christ Church
- ·
- Hastings
- 0.12 mi to center
10.0Exceptional
(21 Reviews)
2 Bedrooms
2 Baths
4 Guests
1443 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $328/Night
7 Nights - US $2,298
Apartment
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(16 Reviews)
2 Bedrooms
2 Baths
4 Guests
1227 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $682/Night
7 Nights - US $4,777
Condo
- Hastings
- ·
- Saint Matthias
- 0.13 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
2000 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $593/Night
7 Nights - US $4,148
Apartment
- Rockley
- ·
- Navy Gardens
- 0.07 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $266/Night
7 Nights - US $1,863
Condo
- Christ Church
- ·
- Hastings
- 0.26 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $223/Night
7 Nights - US $1,564
Condo
- Rockley
- ·
- Marine Gardens
- 0.04 mi to center
10.0Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
1304 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $396/Night
7 Nights - US $2,769
Apartment
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
1666 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,111/Night
7 Nights - US $7,778
Condo
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1720 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $916/Night
7 Nights - US $6,411
Apartment
- Christ Church
- ·
- Rockley
- 0.24 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
615 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $195/Night
7 Nights - US $1,366
Pet-Friendly Vacation Rentals in Cheapside
Over 30+ Pet-Friendly Vacation Rentals in or Near Cheapside
House
- St. Michael
- ·
- Bridgetown
- 1.24 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
11 Guests
1350 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $305/Night
7 Nights - US $2,135
Apartment
- Bridgetown
- ·
- Bayville
- 0.02 mi to center
9.2Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
129.17 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $115/Night
7 Nights - US $805
Apartment
- Christ Church
- ·
- Rockley
- 0.15 mi to center
6.8Good
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $146/Night
7 Nights - US $1,020
Villa
- Christ Church
- ·
- Hastings
- 0.14 mi to center
9.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $644/Night
7 Nights - US $4,507
Resort
- Bridgetown
- ·
- Garrison Historic Area
- 0.30 mi to center
7.8Very Good
(340 Reviews)
1 Bath
34 Guests
165.95 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $307/Night
7 Nights - US $2,150
Apartment
- Christ Church
- ·
- Hastings
- 0.27 mi to center
8.6Fabulous
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $116/Night
7 Nights - US $809
House
- Bridgetown
- ·
- Spring Garden
- 0.17 mi to center
8.6Fabulous
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $372/Night
7 Nights - US $2,603
Apartment
6.0Good
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $126/Night
7 Nights - US $882
House
- Bridgetown
- ·
- Eagle Hall
- 0.19 mi to center
4.0Average
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Internet
- Pet Friendly
- Child Friendly
US $129/Night
7 Nights - US $906
Large Vacation Homes & Villas in Cheapside
Over 109+ Large Vacation Homes & Villas in or Near Cheapside
Villa
- Bridgetown
- ·
- Bayville
- 0.03 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $586/Night
7 Nights - US $4,104
New
Apartment
- St. Michael
- ·
- Bridgetown
- 0.61 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
4 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $75/Night
7 Nights - US $525
House
- Christ Church
- ·
- Hastings
- 0.23 mi to center
6 Bedrooms
5 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $528/Night
7 Nights - US $3,696
Villa
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $873/Night
7 Nights - US $6,113
Apartment
- St. Michael
- ·
- Bridgetown
- 1.13 mi to center
9.4Exceptional
(106 Reviews)
5 Bedrooms
3 Baths
10 Guests
846.76 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $90/Night
7 Nights - US $630
Villa
- Bridgetown
- ·
- Garrison Historic Area
- 0.22 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $420/Night
7 Nights - US $2,942
Villa
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $937/Night
7 Nights - US $6,556
Villa
- Bridgetown
- ·
- Brighton
- 0.27 mi to center
9.8Exceptional
(56 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $241/Night
7 Nights - US $1,686
New
Villa
9.8Exceptional
(19 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $900/Night
7 Nights - US $6,301
Wheelchair Accessible Vacation Homes in Cheapside
Over 166+ Wheelchair Accessible Vacation Homes in or Near Cheapside
Apartment
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
1654 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $961/Night
7 Nights - US $6,727
Hotel
- Christ Church
- ·
- Hastings
- 0.37 mi to center
9.0Exceptional
(85 Reviews)
15 Baths
532.45 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
US $567/Night
7 Nights - US $3,972
Resort
- Hastings
- ·
- Saint Matthias
- 0.10 mi to center
9.2Exceptional
(1005 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
Spa
US $776/Night
7 Nights - US $5,433
Apartment
- Hastings
- ·
- Saint Matthias
- 0.12 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
2046 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $375/Night
7 Nights - US $2,628
Hotel
- Bridgetown
- ·
- Blue Waters
- 0.23 mi to center
8.8Fabulous
(287 Reviews)
4 Baths
430.56 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $142/Night
7 Nights - US $991
Condo
- Hastings
- ·
- Saint Matthias
- 0.16 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $761/Night
7 Nights - US $5,330
Condo
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1720 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $720/Night
7 Nights - US $5,041
Condo
- Bridgetown
- ·
- Brighton
- 0.17 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1247 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $706/Night
7 Nights - US $4,944
Condo
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1720 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $983/Night
7 Nights - US $6,879
Cheapside Resorts and Airbnb Homes Under $200
Over 326+ Cheapside Resorts and Airbnb Homes Under $200
Cottage
- Rockley
- ·
- Marine Gardens
- 0.10 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $194/Night
7 Nights - US $1,355
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
8503.49 ft²
Private Beach- Oceanfront
- Parking
- Ocean View
US $197/Night
7 Nights - US $1,377
Apartment
- Bridgetown
- ·
- Howells
- 0.35 mi to center
9.0Exceptional
(98 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $92/Night
7 Nights - US $647
House
- St. Michael
- ·
- Bridgetown
- 1.59 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $101/Night
7 Nights - US $705
House
- Bridgetown
- ·
- Clapham
- 0.13 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
495.14 ft²
- Parking
- View
- Air Conditioner
- Internet
US $169/Night
7 Nights - US $1,180
Apartment
- Bridgetown
- ·
- Pine Gardens
- 0.18 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $90/Night
7 Nights - US $630
Condo
- Christ Church
- ·
- Hastings
- 0.25 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
2 Baths
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $193/Night
7 Nights - US $1,351
House
- Rockley
- ·
- Navy Gardens
- 0.18 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $128/Night
7 Nights - US $898
New
House
- Rockley
- ·
- Marine Gardens
- 0.04 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $193/Night
7 Nights - US $1,351
Instantly Bookable Vacation Homes in Cheapside
Over 435+ Instantly Bookable Vacation Homes in or Near Cheapside
Apartment
- Bridgetown
- ·
- Bayville
- 0.07 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
5 Guests
1350 ft²
- Parking
- Ocean View
- View
- Kitchen
US $254/Night
7 Nights - US $1,778
US $6,587/Night
7 Nights - US $46,108
House
- St. Michael
- ·
- Bridgetown
- 1.39 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $280/Night
7 Nights - US $1,961
House
- Rockley
- ·
- Marine Gardens
- 0.17 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $205/Night
7 Nights - US $1,437
Apartment
- Hastings
- ·
- Saint Matthias
- 0.12 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $122/Night
7 Nights - US $857
Condo
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1720 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $811/Night
7 Nights - US $5,674
Apartment
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1277 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $715/Night
7 Nights - US $5,005
Apartment
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $416/Night
7 Nights - US $2,910
House
- St. Michael
- ·
- Bridgetown
- 0.81 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $183/Night
7 Nights - US $1,279
Book a Last Minute Place to Stay in Cheapside
About Cheapside Vacation Rentals
Explore over 894 vacation rentals in Cheapside with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Cheapside for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Cheapside. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Cheapside tailored to your preferences. On average, these rentals offer 748.32 ft² of space, and are priced at an average of US $505 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Cheapside at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Show more
Show less
Top Types of Ski Accommodations in Cheapside
| Type | Count |
|---|---|
| Holiday Apartments | 393 |
| Vacation Homes | 192 |
| Villas | 77 |
| Cottages | 24 |
| B&B | 1 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Cheapside
★ Pro Tip: Discover Your Ideal Vacation Rental in Cheapside with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Top Attractions Around Cheapside, BB
Sunski offers a large selection of top attractions around Cheapside . Research things to do on your vacation before you visit Cheapside.
Other Places to Stay in Cheapside, BB
Frequently Asked Questions About Cheapside?
What are the top vacation rentals in Cheapside?
When organizing your trip to Cheapside, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Cheapside. Peruse our collection of highly-rated properties and secure your reservation today.
- South Ocean Villas 203 with breathtaking views
- Almond Palm Apartment
- Private steps down to the beach with stunning ocean views
- Cherry Garden Villa Cottage pool in the desirable Rockley Beach location
- Upper Beachgate - On the Beach.
- Cherry Garden Villa Apartment - private pool in desirable Rockley Beach location
- Luxury spacious condo in the heart of it all
- Best E Villas Prospect
- Stunning New Luxury Beachfront Condo - Allure 202
- Lower Beachgate - On the Beach.
How many vacation rentals have private pools in Cheapside?
Uncover 53 vacation rentals boasting private pools near Cheapside. Explore top-rated RBO homes offering access to a swimming pool:
- Crotona Garden Upper Cottage 1 Bed Apt, Pool, Lush, Tropical, 2 Min Walk to Sea
- Portico 1
- Exclusive Townhouse with Luxury Upgrades and private Pool and amazing Views
- Imagine Villa- Clean & Modern Beachfront 4 bed with Penthouse
Which vacation homes or resorts in Cheapside are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Cheapside. Enjoy great views, locations and save money with SunSki Resorts.™
How many SunSkiResorts vacation rentals or resorts are available in Cheapside?
Discover the ideal vacation rental in Cheapside with SunSki Resorts™. We provide an extensive selection of over 894 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Cheapside.
Map
