Vacation rentals in Enfield

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Top-rated vacation rentals in Enfield

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Top guest favorite
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, 466 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

Superhost
A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.
Home in South Windsor
4.89 out of 5 average rating, 177 reviews

Spacious 3 Bedroom Ranch With Office

Forget your worries in this spacious and serene space with room for 8. The entire first floor is yours to enjoy and there aren’t any shared spaces. Relax in the backyard or on the porch. 2 full bathrooms are yours to relax and enjoy. There’s a freshly remodeled bathroom in the master bedroom with walk in shower and a bathtub in the 2nd bathroom. Fully stocked kitchen awaits your inspiration. Much shopping awaits you and all the store are within 10 minutes away from you. BDL is 20 minutes away,

Guest favorite
A cozy studio space features a spacious bed with a light coverlet and decorative pillows. A neutral rug lies beneath, complementing the wooden flooring. Decorative wall art and plants are displayed throughout, while a workspace with a desk and chair is neatly arranged nearby.
Apartment in Broad Brook
4.89 out of 5 average rating, 114 reviews

Modern Cozy Studio

Experience the perfect stay in this cozy studio, nestled in the heart of Broad Brook. You'll be conveniently close to local restaurants, the Opera House, and just a short drive from Bradley International Airport, Hartford, CT, and Springfield, MA. Plus, we're pet-friendly! Enjoy direct access to Mill Pond and easy ground-level entry. There are no additional cleaning costs. Your comfort is our priority! As an added bonus, a portion of your stay supports St. Jude Children’s Research Hospital!

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 favorite
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 favorite
A cozy living room features a stone fireplace surrounded by purple walls. A wooden table sits at the center, adorned with a decorative bowl. A comfortable sofa and a wooden chair are positioned near the fireplace, complementing the warm ambiance.
Cottage in Windsor
4.9 out of 5 average rating, 206 reviews

In-law apartment in Farmington River Cottage

If you are craving a getaway with a special someone, this space is meticulously clean and an opportunity to practice social distancing while relaxing and enjoying the Farmington River. Only 15 minutes from Bradley airport, 5 minutes from the train and I91. Nature, dining, all within a comfortable drive. You get it all here! Private space with its own entrance, one bedroom and newly updated bathroom, a cozy living room with fireplace in a Garden Level Unit. Off street parking available.

Top guest favorite
Home in West Suffield
4.97 out of 5 average rating, 126 reviews

Linny's - Lakefront Retreat Private Dock & Firepit

🌲🌳 What Guests Love -> -Private waterfront dock -Swimming and lake access -Firepit with serene views -Peaceful morning coffee spot -Family-friendly setup -Fast WiFi for remote work or streaming -Bright open living space -Comfortable bedrooms -Fully equipped kitchen -Great lake views -Smart TV and high-speed internet -Clean, modern bathroom Spend your days on the water and your evenings grilling, relaxing on the dock, or enjoying wine at sunset while the kids play lakeside.

Top guest favorite
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, 147 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 favorite
A welcoming entrance features a maroon front door with glass panes, flanked by a wooden railing. A slight wooden ramp leads up to the door, surrounded by a manicured area of small plants and gravel, creating an inviting first impression.
Home in Feeding Hills
4.89 out of 5 average rating, 1,036 reviews

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Guest favorite
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, 237 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 favorite
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
A serene riverside deck overlooks the calm waters of the Connecticut River. The space features wooden railings and is surrounded by lush greenery, with a few bare trees reflecting the change of seasons. The peaceful landscape offers a quiet spot for relaxation.
Cottage in Enfield
4.84 out of 5 average rating, 191 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!

Popular amenities for Enfield vacation rentals

When is the best time to visit Enfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$27,202 GYDG$26,574 GYDG$26,365 GYDG$29,294 GYDG$29,713 GYDG$31,387 GYDG$32,224 GYDG$32,224 GYDG$31,805 GYDG$34,525 GYDG$30,759 GYDG$29,294 GYD
Avg. temp-3°C-1°C3°C10°C16°C20°C24°C23°C18°C12°C6°C0°C

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 G$2,092 GYD 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 & 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

  • Wi-Fi availability

    50 of Enfield vacation rentals include wi-fi 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!