Stay If You Dare - Vacation Rentals in Pleasant Valley

L&R From US $219
         

1.0 (1 Review)
Bed & Breakfast
L&R
  • Air Conditioner
  • Parking
  • Pool
Family House On Highland Lake with Dock From US $360
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Lakefront Tranquility/Fishermans Delight From US $275
         

10.0 (21 Reviews)
Cottage
  • Parking
  • TV
  • Balcony/Terrace
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove From US $420
         

Luxury Places to Stay in Pleasant Valley

Over 36+ Luxury Places to Stay in or Near Pleasant Valley
Lakefront Escape on Highland From US $1,073
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Charming 2-bedroom apartment with AC, WiFi LAKE VIEWS! From US $427
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Top-Rated Vacation Rentals with a Pool in Pleasant Valley

Over 4+ Top-Rated Vacation Rentals with a Pool in or Near Pleasant Valley
Lakeside Oasis with Hot Tub; 5 min to Ski Mountain! From US $1,308
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
One Bedroom Guest House Nestled in the mountain From US $278
         

8.4 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Pleasant Valley

Over 5+ Pet-Friendly Vacation Rentals in or Near Pleasant Valley
Cherrybrook Hideaway - Book now for autumn colors! From US $330
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lake House on the Cleanest Lake in CT From US $300
         

3.8 (5 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Large Vacation Homes & Villas in Pleasant Valley

Over 3+ Large Vacation Homes & Villas in or Near Pleasant Valley
3 Bedroom Family Friendly Home in Riverton Paradise From US $217
         

8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Pleasant Valley Varoom and Airbnb Places to Stay Under $200

Over 6+ Pleasant Valley Varoom and Airbnb Places to Stay Under $200
Best Outdoors near the Berkshires From US $134
         

9.8 (9 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
RIVERSIDE HOMESTEAD on the Farmington River From US $187
         

9.8 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Getaway for a weekend! From US $94
         

6.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Pleasant Valley

Over 5+ Instantly Bookable Vacation Homes in or Near Pleasant Valley
West Hill Cabin From US $293
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Experience Fall in the Berkshires From US $435
         

New
House
  • Parking
  • Balcony/Terrace
  • Security/Safety
Charming 2-bedroom apartment in welcoming Winsted with WiFi, AC From US $385
         

About Pleasant Valley Vacation Rentals

With more than 45 Pleasant Valley vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Stayifyoudare 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 Pleasant Valley.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Stayifyoudare Pleasant Valley, 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 Pleasant Valley. Places to stay near Pleasant Valley are 622.15 ft² on average, with prices averaging $395 a night.

Stayifyoudare makes it easy and safe to find and compare vacation rentals in Pleasant Valley 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 Pleasant Valley

Type Count
Vacation Homes 29
Holiday Apartments 7
Cottages 6
B&B 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Pleasant Valley

Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare 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 Pleasant Valley.

Weather in Pleasant Valley

View the weather forecast for Pleasant Valley before booking your Pleasant Valley Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F