Vacation rentals in Enfield

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Top-rated vacation rentals in Enfield

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

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Top guest favourite
A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.
Cottage in Becket
4.95 out of 5 average rating, 305 reviews

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

Top guest favourite
A hot tub with bubbling water is showcased under a covered patio, offering a view of the serene lake and surrounding trees. Soft lighting enhances the tranquil setting, while glimpses of the lake's shoreline and distant boats are visible in the background.
Cottage in Southwick
4.98 out of 5 average rating, 150 reviews

Lake Views from Hot Tub Fire Pit & 4 Kayaks

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for a week long getaway with 2 work spaces. 25 minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Top guest favourite
The exterior view features a small wooden cabin surrounded by vibrant green trees. A stone path leads to a seating area, comprising four metal chairs and a table. Inside, the cozy octagonal space is lit by natural light filtering through several windows, showcasing a full-sized bed adorned with a colorful patterned quilt.
Tiny homes in Norwich
4.99 out of 5 average rating, 934 reviews

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Superhost
A bright workspace features a wooden desk with a black chair, positioned against a light-colored wall. Two framed botanical prints are displayed above the desk, complemented by a standing lamp. A mirror reflects the scene, while a potted plant adds a touch of greenery.
Apartment in Windsor Locks
4.83 out of 5 average rating, 192 reviews

Apt near Big E, Six Flags, Bradley airport

Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Top guest favourite
An expansive view of rolling hills and distant mountains is visible through a treeline, with a foreground of manicured green grass and apple trees. The cabin's wooden structure is partially seen on the right, enhancing the connection to nature.
Cabin in Williamsburg
4.97 out of 5 average rating, 116 reviews

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Top guest favourite
A comfortable studio space is highlighted by a plush queen bed adorned with white bedding, positioned beside a cozy fireplace. Soft light is provided by a bedside lamp, while a fan offers air circulation. Neutral tones and warm accents create a welcoming ambiance.
Apartment in Wilbraham
4.99 out of 5 average rating, 145 reviews

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Guest favourite
A serene riverside deck features two striped lounge chairs, positioned for optimal views of the Connecticut River. Lush greenery frames the scene, and flower pots add a touch of elegance. The wooden deck offers a natural and inviting space to relax by the water.
Home in Agawam
4.97 out of 5 average rating, 235 reviews

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Guest favourite
Bungalow in Longmeadow
4.78 out of 5 average rating, 243 reviews

Elegant 3BR Longmeadow Home| Sauna| Near Big E

Welcome to your peaceful Longmeadow retreat—perfect for families visiting loved ones, Springfield events, or trips to The Big E. This charming 3BR bungalow features a wood-burning fireplace, outdoor barrel sauna, private backyard, and uplifting artistic touches. Located across from a quiet park and minutes from Springfield, the MassMutual Center, and Eastern States Exposition, it offers a relaxing place to recharge after a busy day.

Superhost
Cottage in Enfield
4.85 out of 5 average rating, 190 reviews

Hilda’s Riverside Retreat

Amazing Newly renovated Airbnb! Nestled along the meandering, Connecticut River, beautiful veiw! “Just what the doctor ordered”. And just a stone’s throw away from Downtown Springfield, MGM and Hartford. Whether you are visiting the Knowledge Corridor to visit any of the 30+ universities and liberal arts colleges, business or pleasure, This waterfront property is cozy and offers every amenity you left at home!

Top guest favourite
The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.
Guesthouse in Granby
4.98 out of 5 average rating, 903 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Top guest favourite
Apartment in Tolland
4.96 out of 5 average rating, 340 reviews

Cozy studio loft

Cozy studio apartment in a quiet, wooded setting in Tolland, CT—just minutes from I-84 and 15 minutes to UConn. Sleeps 2–4 with a queen bed and optional mattress. Includes full kitchen, bathroom, fast Wi-Fi, private entrance, and easy self check-in. Free Level 2 EV charging and plenty of parking. Ideal for short or extended stays. No pets, no smoking, no parties.

Guest favourite
A bright living area features a dark sofa with multiple cushions, flanked by two patterned chairs. A wooden coffee table is positioned in the center, and a laptop is placed on it. Natural light enters through the two windows, adorned with dark curtains.
Apartment in Enfield
4.99 out of 5 average rating, 313 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

Popular amenities for Enfield vacation rentals

When is the best time to visit Enfield?

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Frequently Asked Questions

  • What are the best places to stay in Enfield?

    Vacation rentals in Enfield's residential neighborhoods are frequently suggested for their quiet setting and proximity to parks or local shops. Areas near the town center make it easy to explore museums and dining spots.

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

    Children frequently enjoy playgrounds, splash pads in parks, and hands-on activities at local museums. Seasonal festivals and indoor play spaces offer variety throughout the year.

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

    Discover locally rooted history at museums, stroll parks with river views, and attend town events with food or music. Enfield has a mix of outdoor spaces, community gatherings, and neighborhood eateries.

  • How is the weather in Enfield?

    Enfield has cold winters around 19–41°F (-7–5°C), with regular snowfall and moderate precipitation. Summer brings warmer temperatures between 64–85°F (18–30°C), perfect for outdoor activities and local festivals.

  • When is the best time to visit Enfield?

    Late spring and early fall are often recommended, with comfortable temperatures around 48–76°F (9–24°C) and fewer crowds. Summer is popular for outdoor activities and local events, while winter brings a quieter atmosphere.

  • What are the best places to visit in Enfield?

    Frequently suggested sites include community parks, historic museums, and riverside paths inviting leisurely walks. Local farmers markets and neighborhood cafes show off the area's welcoming atmosphere.

  • What are some hiking trails in Enfield?

    Enfield has wooded walking paths and scenic trails in local parks for those looking to spend time outdoors. Park areas often recommend gentle hiking options suitable for many skill levels.

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

    Families can explore playgrounds, enjoy picnic spots in local parks, and visit community centers with seasonal events. Indoor activity centers and libraries often create engaging programs for children and adults alike.

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

    Explore historic towns with unique shops, visit nearby nature reserves filled with hiking trails, or enjoy cultural attractions in larger cities around the region. Wineries, rural farmstands, and art galleries make for varied day experiences.

  • Are there any pet friendly accommodations available in Enfield?

    Many vacation rentals in Enfield welcome pets, especially in neighborhoods near parks or walking trails. Hosts often provide pet-friendly amenities and share local tips for exploring with your animal companion.

  • What are some local tips for visiting Enfield?

    Locals often recommend wearing comfortable shoes for park strolls and checking the calendar for community events. Early mornings offer quieter experiences at popular spots, and tasting locally made foods is a welcoming way to connect.

  • What is Enfield known for?

    Enfield is known for its riverside parks, locally rooted history, and community festivals that celebrate the area’s traditions. The town has a balance of suburban character and welcoming neighborhood spaces.

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

    Explore small neighborhood museums sharing local history, pocket parks tucked within residential areas, and craft shops with regional goods. Art installations and murals add an unexpected creative touch around town.

  • What are the best foods to try in Enfield?

    Enfield has locally popular pizza, hearty New England comfort foods like clam chowder, and family-run diners with home-style breakfasts. Bakeries and farmstands share fresh pastries and seasonal produce.

  • What should I bring for a trip to Enfield?

    Pack comfortable clothing for outdoor activities, layers for changing temperatures, and sturdy shoes for walking trails. An umbrella or rain jacket is useful, particularly during spring and fall when showers are common.

  • What is the nightlife in Enfield like?

    Enfield has casual bars, locally owned restaurants, and community gathering spots that make for relaxed evenings. Live music or special events can sometimes be found at popular venues around town.

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

    Enfield has summer celebrations centered around the Fourth of July, including community fairs, outdoor music, and fireworks. Throughout the year, holiday parades and seasonal cultural events bring residents together for food, music, and local traditions.

  • Are there family friendly vacation rentals in Enfield?

    Enfield has vacation rentals in neighborhoods with space for families, including options with kitchens, play areas, or nearby parks. Many hosts accommodate children and offer amenities for a comfortable stay.

Quick stats about vacation rentals in Enfield

  • Total vacation rentals

    Explore 60 vacation rentals in Enfield

  • Nightly prices starting at

    Enfield vacation rentals start at $14 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,200 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Enfield vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Enfield rentals

  • 4.8 Average rating

    Enfield stays are highly rated by guests—averaging 4.8 out of 5!