Middlefield Vacation Rentals with Pools
1980 ft²
8 Guests
4 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $281/Night
For 7 Nights US $1,968
2700 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Spa
- Fireplace/Heating
US $185/Night
For 7 Nights US $1,295
1800 ft²
4 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $210/Night
For 7 Nights US $1,470
650 ft²
4 Guests
3 Bedrooms
1 Bathroom
Ocean View
Cottage
- Ocean View
- Balcony/Terrace
- View
US $241/Night
For 7 Nights US $1,688
3056.95 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $263/Night
For 7 Nights US $1,841
1170 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $457/Night
For 7 Nights US $3,198
2002.09 ft²
6 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Pet Friendly
- Parking
- Internet
US $152/Night
For 7 Nights US $1,064
2000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Parking
US $160/Night
For 7 Nights US $1,117
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
House
- Internet
- Child Friendly
- Barbecue/Outdoor Cooking
US $78/Night
For 7 Nights US $546
1650 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $225/Night
For 7 Nights US $1,575
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $248/Night
For 7 Nights US $1,739
7 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $426/Night
For 7 Nights US $2,982
Why Choose Rent By Owner for your Middlefield Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Middlefield
How to Book Your Middlefield Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middlefield
Common Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Middlefield, MA
Skyline Trail
Middlefield Vacation Rentals with Pools Frequently Asked Questions
1. What are the top Rentals With Pools in Middlefield?
There are a lot of options in Middlefield. If you plan on staying in the Middlefield area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Rentals With Pools in Middlefield:
- Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
- Remote and Relaxing Cabin in the Berkshires
- Lakefront Cottage In The Berkshires In Western Massachusetts
- Beautiful Timber Frame Home in the Berkshires /Available for Long Term
- 1840's Ship Captain's Farm Estate, 6-10 guests
- Quintessential 1860's Berkshire farmhouse with mountain views on 30 acres.
- Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
- Private Lake Cottage on 3 acres w/350 sq. ft. deckn
- Cozy Berkshires Vacation Rental Near Hiking!
- Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
2. How many Rentals With Pools are available in Middlefield?
Currently, the total number of properties listed by RBO in 2026 is over 3 in the Middlefield area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Middlefield.
More Rentals You May Like Near Middlefield
2700 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
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8 Guests
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- Hot Tub
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10 Guests
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- Fireplace/Heating
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6 Guests
4 Bedrooms
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- Fireplace/Heating
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3300 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
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US $883/Night
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1400 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $458/Night
For 7 Nights US $3,208
14 Guests
7 Bedrooms
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Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,718/Night
For 7 Nights US $12,023
6 Guests
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Family Friendly
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- Fireplace/Heating
- Kitchen
- Parking
US $224/Night
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7 Guests
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2 Bathrooms
Ocean View
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- Spa
- Fireplace/Heating
- Ocean View
US $339/Night
For 7 Nights US $2,370
