
Vacation rentals with a pool in Litchfield County
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Top-rated rentals with a pool in Litchfield County
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House rentals with a pool

Beautiful Country Farmhouse w/ Pool
This is a beautiful, cozy and tasteful home. We loved the contrast between the original 300 year old farm beautifully maintained and renovated and the newer rooms. Kitchen was great and the fireplace worked wonderfully. Wifi and office space were perfect to get a few hours of work done. Had a great week skiing in nearby Mohawk and visiting Litchfield and Bantam. It was useful to inquire about the lay out and steep stairs. Daire was super responsive and helpful throughout our stay. We had a wonderful time. Thanks for sharing your home!

2 homes in one (in-law design) w/salt water pool
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!

Chic Modern Farmhouse in Rhinebeck with pool
We loved our stay. The house has a lovely open floor plan with lots of light streaming in. The renovations are very recent and everything is spotless and gleaming. The king-sized bed in the master bedroom is extremely comfortable and the wraparound deck would be delightful when the weather is warm and sunny. The setting is peaceful and the location is ideal, midway between Rhinebeck and Red Hook villages, with easy access to everything those towns have to offer. We would happily return to this lovely house.

Stunningly Designed Luxury Home w/ Pool & Hot Tub
We had an amazing relaxing weekend. The beds are comfy, pool heated, quiet serene area. All around perfect weekend getaway. The house was clean and had everything we could have possibly needed.

Enchanted Escape | POOL, LAKE, Concierge Services
We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.

Amazing Oasis Private Pool, BBQ, Pool Table.
This house was perfect for my family to stay for the weekend so we could attend a family wedding. Wish the weather was nicer so we could have enjoyed the pool on our down time. But house was perfect!! Soo cute and Glenda responded very fast. She was so helpful! I would highly recommend this place to anyone and everyone!!

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature
We had an amazing stay! David was quick to respond with any questions I had and even came out to hook up the propane tank for the heated pool. I saw in previous reviews about the tricky driveway but David’s description of it is perfectly accurate and not any trouble, just a little steep but nothing super tricky to deal with! The house has a beautiful setup and view, very clean and so much space. Even though it was cold and rainy we had the most fun and peaceful stay at this home. The bride of the bachelorette group said she wants to book with David on her own just for another stay/get-a-way! Highly recommend this beautiful space!
Condo rentals with a pool

Watersedge resort time share Westbrook ct
Andrew’s place was awesome. Just steps to a beautiful pool and the ocean! Couldn’t have asked for a better place.

Quaint spacious unit, A+ location
Will was pleasant, easy to reach for quick fixes and very communicative! He answered any questions we had and was incredibly helpful with locating the apartment as the map location was a little off. The apartment was beautiful, well decorated and clean! We stayed for 16 days and had little to no issues. I am confident anyone else would find this place to be worth the price!

Beautiful 2 bedrooms/ 2 bath Condo
Sheryl was great. I was in town for a conference and my schedule got thrown off by traffic on 95. She was very understanding and flexible with making my arrival time work. Once we met to get keys and a quick tour of the place she remained a phone call away but otherwise left us to enjoy the space. The other inhabitants of the place were very laid back and nice - that being said I was so busy with a conference that I was barely around. Not the Ritz but a HUGE savings over staying at any hotel downtown even if it's not right downtown. Splurge on some cabs and you are still saving money.

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

Cozy and charming retreat in quiet area of Wlfd.
Cristina's home was great for our stay! She was extremely helpful even before we checked in, providing clear instructions on where to park and the location of the entrance. She even left out some toys for our son to play with during our time there. It's small space, but what we needed and exactly as described in the listing. We would absolutely stay here again, when we come back to the area!

Holiday Inn Club/ Oak and Spruce, Berkshires
This was a perfect place to stay with my kids for a weekend at Tanglewood. We used the Lions Gate parking at Tanglewood and got back to the place in 15 min! Easy
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- Fairfield Beach
- Yale University
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Seaside Beach
- Bushnell Park
- Calf Pasture Beach
- Jennings Beach
- Silver Sands Beach
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Walkway Over the Hudson State Historic Park
- Sherwood Island State Park
- Bayview Beach
- Hudson Highlands State Park
- Kent Falls State Park
- Wildemere Beach
- South Pine Creek Beach
- Marvin Beach
- The Connecticut Golf Club