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Holiday rentals in Bloomfield

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Top-rated holiday rentals in Bloomfield

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

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Chalet in Goshen

4.89 out of 5 average rating, 131 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

Guest favourite

Home in Morris

4.86 out of 5 average rating, 148 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Home in Litchfield

4.84 out of 5 average rating, 350 reviews

Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ

Enjoy the comfort of home with air conditioning, heating, dedicated workspace, TV, and Wi-Fi. Cook your meals in the fully-stocked kitchen with all the essentials. Pamper yourself in the private bathtub or shower with provided body soap, shampoo and conditioner. Relax in the hot tub or lounge in the backyard with an outdoor dining area, bbq, patio, and fire pit. 3 Min - Litchfield Town 4 Min - Arethusa Dairy farm 5 Min - White Memorial Conservation Center 16 Min - Mohawk Mountain Ski Area

Guest favourite

Home in Farmington

5 out of 5 average rating, 60 reviews

Lake Escape: Lake Cottage Charm, Lake Front, AC

Direct lakefront access with gorgeous views on a private lake. This beautiful 1930's lakefront cottage was fully renovated and reimagined by its owners in 2021. Custom architectural trim and details can be found throughout blending this homes' heritage with modern amenities. 2 bedrooms, eat-in kitchen and window seat nook, 2 full baths, custom barn doors and cabinetry, a reimagined sunroom, beautiful views on 100' of accessible lake frontage with outdoor patio, 1 mile from town center.

Guest favourite

Home in Oxford

4.97 out of 5 average rating, 37 reviews

Lakefront Oasis - Getaway to this Oxford Treasure!

Relax with family and friends at this breathtaking lake front home. Peaceful setting with beautiful views of Swan Lake. Updated bedrooms, completely renovated bathrooms and all new kitchen appliances. A kayak and paddleboard await your next adventure. A brand new dock was installed for boating, fishing and swimming right from our backyard. Just a few minutes from the town center grocery store, restaurants, amusement parks, skiing and more. Dogs considered on a case by case basis!

Guest favourite

Cottage in Plymouth

4.95 out of 5 average rating, 100 reviews

Lakefront Cozy Oasis 2BR w/ stunning sunset views

Come stay @cozyoasisct for sunset hour and enjoy dramatic views from the comfort of the living room, kitchen, or outdoor patio. Our private community lake is great for swimming, fishing, kayaking, bird watching and ice skating in the winter. Great for your next getaway, relaxing weekend, or just a place to work remotely. The property is equipped with kayaks, shuffleboard, fast WiFi, deskspace, Smart TVs, and a full kitchen. We can’t wait to host you! We're Pet Friendly

Guest favourite

Home in Otis

4.9 out of 5 average rating, 51 reviews

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

Bungalow in Longmeadow

4.76 out of 5 average rating, 202 reviews

Artist Longmeadow 3bdrmHOUSE with OUTDOOR SAUNA

Welcome to my sanctuary of creativity, culture, and connection in Longmeadow, where hospitality is my way of sharing love, joy, and a glimpse into my Haitian heritage. This inviting space is designed to feel like home while inspiring your stay. Relax in the outdoor sauna, fire up the BBQ, or simply unwind in the quiet backyard. Across from a serene park, this is a retreat to recharge, connect, and create lasting memories. Self-check-in makes arriving a breeze.

Guest favourite

Home in Otis

4.92 out of 5 average rating, 147 reviews

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Guest favourite

Home in Canton

4.99 out of 5 average rating, 97 reviews

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view!Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful yearround!

Guest favourite

Guest house in East Hampton

4.93 out of 5 average rating, 41 reviews

Family-Friendly Lakeside Cottage

Newly renovated lakeside cottage with stunning views. 2 bedrooms with king beds and a pull-out couch, 1.5 bathrooms - 30 second walk to the lake - Fully furnished and equipped - Private rock patio with picnic table and grill - Washer and dryer in unit - Desk for working from home - 2 Kayaks and 2 paddle boards are available for use - Short walk or drive to restaurants, and shops Perfect for romantic getaways, family vacations, or visiting family locally.

Guest favourite

Home in Otis

4.96 out of 5 average rating, 105 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

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Popular amenities for Bloomfield holiday rentals

Free parking on premises

Air conditioning

Stay near Bloomfield's top sights

Heublein Tower37 locals recommend

Talcott Mountain State Park34 locals recommend

Millwright's Restaurant and Tavern15 locals recommend

Abigail's Grille and Wine Bar14 locals recommend

Harvest Cafe & Bakery12 locals recommend

Plan B Burger Bar - Simsbury11 locals recommend

Other great holiday rentals in Bloomfield

Home in Southbury

4.87 out of 5 average rating, 45 reviews

Cozy Nature Retreat at Chateau Madeux

Guest favourite

Guest house in Southbury

4.93 out of 5 average rating, 313 reviews

Charming Guest Cottage with Modern Amenities

Guest favourite

Home in Andover

5 out of 5 average rating, 51 reviews

Spacious Classic Lakefront Home with jet tub

Guest favourite

Cottage in Hebron

4.89 out of 5 average rating, 117 reviews

Welcome to The Holly at Amston Lake

Guest favourite

Guest suite in Wolcott

4.9 out of 5 average rating, 42 reviews

Modern cozy, pet friendly

Guest favourite

Cabin in Sandisfield

4.99 out of 5 average rating, 98 reviews

Berkshires Cabin in Woods with Mountain Views

Guest favourite

Home in Farmington

5 out of 5 average rating, 51 reviews

Water front home with lake amenities

Guest favourite

Home in Middletown

4.95 out of 5 average rating, 39 reviews

Hot Tub and pool Home away from home

Quick stats about holiday rentals in Bloomfield

Total rentals
60 properties
Nightly prices starting at
₹1,699 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Destinations to explore