Holiday rentals in Glastonbury

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Top-rated holiday rentals in Glastonbury

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A striking octagonal home is illuminated at dusk, showcasing wrap-around glass windows that blend with the surrounding woodland. The exterior features natural stone accents, and a warm glow from a light at the entrance creates a welcoming ambiance amidst a snowy landscape.
Chalet in Otis
4.95 out of 5 average rating, 469 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Top guest favourite
A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.
Guest house in Portland
4.98 out of 5 average rating, 323 reviews

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Top guest favourite
The spacious studio features a queen-sized bed with a patterned duvet, a comfortable futon, two chairs, and a dining table. A gas fireplace adds warmth, while natural light fills the room through two windows, complemented by light, flowing curtains.
Guest suite in Wethersfield
4.99 out of 5 average rating, 367 reviews

Bright, clean studio in charming Old Wethersfield

Clean, bright studio apartment in the charming village of Old Wethersfield. Stroll to cafes, village green, historic homes and museums. Minutes from I-91 with easy commuting access to downtown Hartford, business and tourist sites, universities, and Hartford Hospital/CCMC. The studio is an in-law suite above our garage. It is attached to our home but has its own keyed entrance. It has a full kitchen, bathroom with shower over tub, closet, queen-sized bed, kitchen table/chairs, and workspace.

Top guest favourite
A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.
Home in East Haddam
4.93 out of 5 average rating, 330 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Guest favourite
A comfortable sleeping area features a dark tufted headboard and a soft, neatly arranged bedding with multiple pillows. A lamp is positioned on a bedside table, while a floor lamp provides additional light. A floral wall art piece adds a subtle touch above the bed.
Home in Manchester
4.94 out of 5 average rating, 236 reviews

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This spacious home includes central air, an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large, newly renovated bathroom with spa like jets. His and hers closets. Beautiful fully stocked kitchenette, 2 large screen Smart TVs, 55 inch in living room, 42 inch in bedroom, Free WiFi, dining for 6, all for the comfort and convenience of our guests.

Top guest favourite
A renovated red barn is showcased, featuring a gray roof and multiple white-framed windows. The surrounding area includes a well-maintained grassy landscape, with trees in the backdrop under an overcast sky.
Guest house in Glastonbury
4.95 out of 5 average rating, 165 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Guest favourite
An open living space showcases a wooden table with candles, surrounded by wooden chairs. A white sofa with decorative cushions is positioned next to a reddish armchair. A coffee table sits central, with a small plant atop a patterned rug. Light illuminates the cozy atmosphere.
Flat in Glastonbury
4.89 out of 5 average rating, 454 reviews

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

Top guest favourite
The farmhouse is depicted with a well-maintained exterior, featuring a symmetrical design and light-colored siding. Vibrant purple and pink flowers bloom in front, adding color to the landscape. A rustic barn is visible in the background, surrounded by lush greenery and a clear blue sky.
Farm stay in Glastonbury
4.96 out of 5 average rating, 112 reviews

Classic Farm House on a Working Farm & Vineyard

This quaint farmhouse will be your home away from home. Enjoy the scenery and explore local attractions. The farm house is situated just feet from Joseph Preli Farm and Winery (also owners of the farmhouse) with its bountiful grapevines, fruits and vegetables. The farm and vineyard is known for it's old-world Italian charm. Family owned for 100 years, they respect history by using traditional farming methods and antique tractors. See updates about the farm and winery at @jprelifarm

Guest favourite
Flat in Manchester
4.96 out of 5 average rating, 141 reviews

Peaceful Pet-Friendly Retreat Near Hartford

Welcome to your home away from home located steps away from downtown Manchester CT! ✔ Private entrance
✔ 1 comfortable bedroom & full bathroom
✔ Fast Wi-Fi for work and entertainment
✔ In-unit washer & dryer
✔ Complimentary coffee
✔ Pet-friendly accommodations
✔ Backyard access
✔ Quiet, residential setting Conveniently located close enough to major events but in a quaint downtown area making it prefect for short or long term stays.

Top guest favourite
The exterior of a colonial barn-style apartment is shown, featuring a stone chimney and a combination of red siding and a gray roof. Lush greenery surrounds the entrance, which includes large glass windows and a welcoming door. A grassy area is visible in the foreground.
Guest house in Glastonbury
4.93 out of 5 average rating, 230 reviews

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

Top guest favourite
The treehouse is elevated on wooden stilts, surrounded by vibrant autumn foliage. Large windows reflect warm light, showcasing a rustic wooden exterior. A staircase leads up to the entrance, inviting guests to explore this serene retreat among the trees.
Treehouse in Willington
4.92 out of 5 average rating, 529 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)

Guest favourite
Tiny home in East Lyme
4.99 out of 5 average rating, 150 reviews

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Popular amenities for Glastonbury holiday rentals

When is the best time to visit Glastonbury?

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Frequently Asked Questions

  • What are the best places to stay in Glastonbury?

    Staying near Glastonbury Center connects you with restaurants, shops, and community spaces. If you prefer a quieter setting, look for vacation rentals around rural or wooded neighborhoods.

  • What are the best things to do in Glastonbury with kids?

    Explore Glastonbury's parks, visit the family-friendly farms, and enjoy hands-on activities at local museums or community centers. Seasonal events with crafts and games are also frequently suggested for children.

  • What are some of the best things to do in Glastonbury?

    Explore Cotton Hollow Preserve's trails, take in local history at the Glastonbury Historical Society, and experience community markets or riverfront parks. Seasonal festivals and apple-picking are also frequently suggested.

  • How is the weather in Glastonbury?

    Glastonbury has cold winters around 19–35°F (-7–2°C) and warm summers reaching 64–85°F (18–30°C). Spring and fall are milder, with changing foliage and increased rainfall, making layers and a light jacket helpful.

  • When is the best time to visit Glastonbury?

    Late spring through early fall is often recommended for a visit to Glastonbury, as temperatures are mild, and local parks and outdoor activities are accessible. Seasonal events and greenery bring extra vibrancy to the town during this period.

  • What are the best places to visit in Glastonbury?

    Explore Glastonbury Center for local shops and dining, the Connecticut River for waterfront walks, and Cotton Hollow Preserve for a natural retreat. Historic sites and inviting parks are also frequently suggested by visitors.

  • What are some hiking trails in Glastonbury?

    Glastonbury has trails like those at Cotton Hollow Preserve, Minnechaug Mountain, and Buckingham Reservoir, where you can explore forested paths and streamside scenery. These spots provide a chance to connect with local nature and spot wildlife.

  • What are some family activities we can do in Glastonbury?

    Families can enjoy playgrounds in town parks, interactive visits to local farms, and participating in seasonal crafts or outdoor movie nights hosted at community centers. Exploring the Connecticut River area is frequently suggested for nature outings.

  • What are some of the best day trip ideas from Glastonbury?

    Explore nearby historic towns, spend time along the Connecticut River, or visit nature preserves for hiking and wildlife observation. Many guests also enjoy discovering regional farms, vineyards, or art galleries around the area.

  • Are there any pet friendly accommodations available in Glastonbury?

    Many vacation rentals in Glastonbury are pet friendly, especially those located near parks or open spaces. Checking listing details for pet policies and local amenities can support a comfortable stay with your companion.

  • What are some local tips for visiting Glastonbury?

    Consider visiting during seasonal markets or festivals to experience local crafts and foods. Many outdoor areas in Glastonbury are popular for picnicking, so bringing a blanket and reusable water bottle can enhance your day.

  • What is Glastonbury known for?

    Glastonbury is known for its apple orchards, historic architecture, and vibrant community events like the Apple Harvest Festival. Naturally scenic areas and preserved open spaces are also central to its character.

  • What are the best hidden gems to explore in Glastonbury?

    Glastonbury has tranquil nature trails such as Minnechaug Mountain, along with historic districts and locally owned shops around Glastonbury Center that draw visitors seeking quieter experiences. Art galleries and community parks are also frequently suggested for those interested in local culture.

  • What are the best foods to try in Glastonbury?

    Glastonbury has locally grown apples, cider donuts, and dishes featuring New England seafood on many menus. Farm-to-table cafes and family-owned bakeries showcase regional ingredients and homemade treats.

  • What should I bring for a trip to Glastonbury?

    Pack comfortable walking shoes for trails, layers to adjust to changing temperatures, and a rain jacket for unexpected showers. Bringing a reusable water bottle and sun protection is also frequently suggested.

  • What is the nightlife in Glastonbury like?

    Glastonbury's nightlife features cozy pubs, locally rooted restaurants, and occasional live music venues. Evenings are often centered around relaxed dining, craft beverages, and small community gatherings.

  • What are the most popular events or festivals in Glastonbury?

    The Apple Harvest Festival in autumn is often recommended, drawing visitors for food, crafts, and family activities. Seasonal farmers markets and summer concerts in the park are other well-attended events.

  • Are there family friendly vacation rentals in Glastonbury?

    Glastonbury has vacation rentals that welcome families, with options near parks and community spaces. Many homes feature kitchens and flexible living areas to accommodate groups of various sizes.

Quick stats about holiday rentals in Glastonbury

  • Total holiday rentals

    Explore 60 holiday rentals in Glastonbury

  • Nightly prices starting at

    Glastonbury holiday rentals start at €35 per night before taxes and fees

  • Verified guest reviews

    Over 2,870 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Glastonbury holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Glastonbury rentals

  • 4.8 Average rating

    Glastonbury stays are highly rated by guests – averaging 4.8 out of 5!