Airbnb your place

Holiday rentals in Bloomfield

Find and book unique accommodation on Airbnb

When results are available, navigate with the up and down arrow keys or explore by touch or swipe gestures.

Top-rated holiday rentals in Bloomfield

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

Superhost

Home in Great Barrington

4.88 out of 5 average rating, 101 reviews

Great Barrington, Cabin Sleeps 14, Walk To Town

You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 350 feet walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more! Short walk to a great lake with a beach area - bring your dogs and family to swim in or walk around and enjoy the nature reservation!

Guest favourite

Holiday home in Warren

4.98 out of 5 average rating, 154 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Superhost

Chalet in Goshen

4.89 out of 5 average rating, 134 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.

Superhost

Cottage in Great Barrington

4.83 out of 5 average rating, 35 reviews

THE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!

It's all about the location and the interior renovation that makes our cottage stands out. Only 5 min to Catamount Ski Mountain, 10 min from Butternut and Only 5 min from town of Great Barrington with dining experience, Bowling ally, movie theater. Summer - for swim and boating - 5 min from Mansfield (swim) and 20 min to stockbridge bowl (boating). 5bd, 4 bath, 2 living rooms, fire place, Hot tub, fire pit, nesting on a 5 acre wooded forest, for complete privacy. (back yard is fenced) .

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

Flat in East Lyme

4.97 out of 5 average rating, 219 reviews

Brand New Direct Lakefront - Panoramic Sunsets

Completely remodeled lakefront apartment offering sweeping views of Pattagansett Lake. Open floor plan, fully equipped kitchen and massive deck make for an ideal gathering place to catch up with family or friends. All three spacious bedrooms offer comfy queen memory foam mattresses, fresh linens and UHD smart TVs. Two full bathrooms, high speed internet and in-unit laundry. Picturesque natural setting yet close to town amenities, restaurants, beaches, casino and area attractions.

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

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.

Guest favourite

Home in Sheffield

4.9 out of 5 average rating, 115 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Rental #1 has 2 bedrooms, a FULLY EQUIPPED KITCHEN and it is SUPERCLEAN! (ALSO SEE THE 1 BEDROOM LISTING #2!) We are conveniently located in between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Two Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favourite

Home in Canton

4.99 out of 5 average rating, 101 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 Brimfield

4.94 out of 5 average rating, 160 reviews

Brimfield Lakeside Home Away from Home

Renovated Brimfield Lakeside Home: minutes to downtown Brimfield & Sturbridge offers two bedrooms plus additional upstairs loft sleeping area, one bath & sleeps six. We are a year round property located in a quiet cove on beautiful Little Alum Pond in Brimfield, Massachusetts. Extremely tranquil setting, yet plenty of great restaurants and shopping are just minutes away.

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Bloomfield holiday rentals

Kitchen
Wifi
Pool
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

Guest favourite

Guest house in Southbury

4.93 out of 5 average rating, 318 reviews

Charming Guest Cottage with Modern Amenities

Superhost

Flat in Great Barrington

4.78 out of 5 average rating, 18 reviews

Writer's retreat: study, books, fireplace (Ecobnb)

Guest favourite

Home in Granby

5 out of 5 average rating, 6 reviews

Lake house retreat Granby CT

Guest favourite

Home in Andover

5 out of 5 average rating, 54 reviews

Spacious Classic Lakefront Home with jet tub

Superhost

Cabin in Lebanon

4.86 out of 5 average rating, 14 reviews

Casa Lago

Guest favourite

Home in Otis

4.92 out of 5 average rating, 149 reviews

The Pinnacle House at Otis Ridge Ski Area!

Guest favourite

Bungalow in Old Lyme

4.94 out of 5 average rating, 295 reviews

Pet Friendly Bungalow!!!

Guest favourite

Home in Tolland

5 out of 5 average rating, 26 reviews

Lakefront Retreat at Porcupine Place

Show all

Quick stats about holiday rentals in Bloomfield

  • Total rentals

    60 properties

  • Nightly prices starting at

    ₹1,733 before taxes and fees

  • Total number of reviews

    2.1K 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