House vacation rentals in Glastonbury

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Popular amenities for Glastonbury house rentals

House rentals with a pool

Superhost
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars7 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars4 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Guest favorite
A serene swimming pool is surrounded by well-maintained greenery, with lounge chairs placed along the deck. Large blue umbrellas provide shade, enhancing the outdoor space suitable for relaxation. A stone wall borders the area, adding a natural touch.
Home in Woodstock
4.94 out of 5 average rating, 235 reviews

Cedar Ridge: House or House+Apartment

SuzanneRating, 5 stars1 month ago
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!
Top guest favorite
The outdoor area features a large in-ground pool surrounded by a fence, with lounge chairs and shaded umbrellas. A spacious wooden deck is visible, along with seating and a small shed. The lush greenery of the backyard complements the serene setting.
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 months ago
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!
Guest favorite
A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Guest favorite
Home in Montville
4.94 out of 5 average rating, 151 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

ElizabethRating, 5 stars2 weeks ago
It was a Beautiful and a comfortable home, definitely will recommend to friends and family
Guest favorite
A cozy living room features exposed wooden beams and warm wood-paneled walls. A stone fireplace is centrally located, with a basket of wood beside it. A rug with rich colors lays under a wooden table, surrounded by comfortable seating, inviting a relaxed atmosphere.
Home in Litchfield
4.93 out of 5 average rating, 185 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

TessaRating, 5 stars1 week ago
This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!
Guest favorite
A vibrant backyard features a spacious pool with clear blue water, complemented by a wooden deck and a shaded seating area under an umbrella. The two-story house stands in the background, surrounded by greenery, creating a peaceful outdoor environment.
Home in Montville
4.95 out of 5 average rating, 148 reviews

Casino Stay & Play House

AmandaRating, 5 stars2 weeks ago
Place was nice and comfy and he was very responsive.

Weekly house rentals

Superhost
A wooden pathway leads through sandy terrain, flanked by low vegetation. The scene is set against a clear blue sky, creating a serene atmosphere that guides visitors toward the shoreline.
Home in Westbrook
4.86 out of 5 average rating, 194 reviews

Family-Friendly Cottage by The Shore

TristanRating, 5 stars6 days ago
I had a nice, overnight stay at Marie's place. All was as described and the instructions for everything were spot on. Comfortable & convenient stay, would visit again!
Guest favorite
A blue-brick exterior is complemented by a landscaped yard featuring two lounge chairs with light blue cushions. A dining area with an umbrella sits adjacent to the building, while stone pathways lead to the entrance flanked by greenery.
Home in Warren
4.94 out of 5 average rating, 108 reviews

Litchfield County Getaway

DemianRating, 5 stars4 months ago
Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend
Guest favorite
A spacious outdoor deck features woven seating and a glass-topped table, overlooking the tranquil water. Sunlight casts shadows on the wooden surface, creating a relaxing atmosphere. Nearby, the waterfront and boats are visible, enhancing the coastal setting.
Home in Groton
4.95 out of 5 average rating, 192 reviews

True Ocean Front Vacationing - Groton/Mystic

KellyRating, 5 stars2 weeks ago
The pictures don't do this place justice! The home itself is gorgeous and the view is stunning. The neighborhood is peaceful and it was perfect for me and four friends to stay the weekend.
Guest favorite
A bright bedroom is presented with a spacious bed, accented by a light-colored comforter. A wooden dresser and a bedside lamp add to the decor. Natural light streams through two windows with light curtains, providing a serene atmosphere.
Home in New Britain
4.89 out of 5 average rating, 104 reviews

5•Star CapeCodStyle Gem with Bedroom on the Main

ErikaRating, 5 stars1 week ago
We had a short stay at Chana‘s place, but everything was perfect for our family. We will definitely book again and recommend to others. Thank you Chana.
Guest favorite
Home in Madison
4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars6 months ago
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.
Guest favorite
The exterior of the house features blue siding with white trim and a welcoming red front door. A small porch is adorned with an American flag. Surrounding greenery and a gravel pathway lead to the entrance, with trees providing a natural backdrop.
Home in Sturbridge
4.96 out of 5 average rating, 168 reviews

Cedar Lake 3 Bed 3 1/2 Bath Home Sturbridge MA

JillRating, 5 stars6 months ago
This was our second time to stay. It had a gorgeous view surrounded by beautiful trees. It was so peaceful and relaxing with everything we needed. James is so easy to work with and very responsive. Highly recommended!
Top guest favorite
A two-story brick house features a spacious covered porch adorned with planters and an American flag. The entrance is framed by two white doors and decorative accents. Lush greenery and small statues are placed along the walkway, enhancing the welcoming façade.
Home in Holyoke
4.97 out of 5 average rating, 327 reviews

Explore Holyoke from this charming 3 Bedroom house

KimRating, 5 stars2 weeks ago
Everything was perfect! It was a great location for us as we were in town for a Cheer Competition! Joseph met us at the door. Everything was as described and they had everything you could possibly need in case something was forgotten! If we are ever back in the area we will try to stay here again!
Guest favorite
A bright living area features a large flat-screen TV mounted on a white console. Two colorful armchairs and a brown leather couch surround a wooden coffee table, all set on a blue area rug. Light streams in through a window, enhancing the cozy atmosphere.
Home in East Hampton
4.92 out of 5 average rating, 93 reviews

Clean private home near Lake Pocotopaug!

CathyRating, 5 stars3 months ago
I highly recommend this property. It was perfect for our Christmas visit with family. The furniture and beds were very comfortable. We truly enjoyed our stay in East Hampton. We will be back!

Private house rentals

Guest favorite
The exterior of the house features a multi-level deck and abundant autumn foliage in vibrant colors covering the ground. Two decorative benches are situated in the foreground, offering a tranquil spot to enjoy the surrounding nature.
Home in Chester
4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

TimRating, 5 stars6 months ago
We'd been looking forward to coming back to The Recycle House since we first stayed there in 2022. Safe to say it was just as we remembered it...great house, great location, wonderful community. Looking forwarded to returning.
Guest favorite
A light-filled living area features a sofa adorned with green and textured throw pillows. Two stylish chairs complement a round coffee table, and a large bookshelf showcases a collection of books and decorative items. A vibrant area rug covers the wooden floor.
Home in Monterey
4.97 out of 5 average rating, 34 reviews

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

GallianeRating, 5 stars2 months ago
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.
Guest favorite
The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars3 weeks ago
It was wonderful stay and I’d go back anytime
Guest favorite
The white estate is framed by bare trees, showcasing a combination of traditional architecture and natural surroundings. A serene lawn is visible in the foreground, with stone walls adding rustic charm. Soft lighting illuminates the porch, creating a welcoming atmosphere.
Home in East Haddam
5 out of 5 average rating, 25 reviews

Elegant Countryside Estate

AnjaliRating, 5 stars4 months ago
Spent a wonderful Thanksgiving weekend at Travis' place with my husband and two young daughters. The house is beautifully appointed and so cozy. We played games by the fire, watched a movie in the cozy tv room, and made and enjoyed lovely meals in the kitchen. The house is even more magical than it looks in the photos, and we certainly hope to be back.
Guest favorite
A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Guest favorite
A modern kitchen features sleek black cabinetry and stainless steel appliances. A large island with bar seating is centered, adorned with a vase of fresh flowers. Natural light floods in through the windows, and a sliding glass door leads to the outdoor deck.
Home in Lyme
4.92 out of 5 average rating, 330 reviews

Stunning, peaceful and private home

KimRating, 5 stars1 week ago
The house was great and we were able to get Ubers to go to dinner. Beautiful house and stocked with everything you would need. We were on a girls weekend and had trouble with the locks but we just used the key. It could have just been us. We had a wonderful time and enjoyed the home.
Guest favorite
The exterior of the house presents a charming two-story design, surrounded by a spacious yard featuring trees and blooming shrubs. A wide driveway leads to a two-car garage, while the house's yellow facade and gray roof create a welcoming appearance.
Home in Bloomfield
4.96 out of 5 average rating, 118 reviews

Spacious Charming New England Cape

JesseRating, 5 stars1 week ago
This is the second time time we've stayed at Carol's place. It's spacious, comfortable, with plenty of open rooms. The kitchen is extremely well stocked. This is becoming our yearly must-stay place!
Top guest favorite
A charming beach cottage is showcased, featuring a light-colored exterior and a welcoming front porch adorned with potted plants. Large windows allow natural light to flood the interior. The surrounding area includes a gravel driveway and mature trees with autumn foliage.
Home in Woodmont
4.92 out of 5 average rating, 254 reviews

Bright and Breezy Cottage by the Sea

LucinaeRating, 5 stars6 days ago
Anne was an amazing host! The house was beautiful and very roomy! The backyard was amazing as well! 10/10 experience

Quick stats about house rentals in Glastonbury

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    770 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore