Family-friendly holiday rentals in Bloomfield

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Top-rated family-friendly rentals in Bloomfield

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Guest suite in Granby

4.91 out of 5 average rating, 144 reviews

Whole place,staycation,3 bedrooms, spacious area

ENTIRE LIVING SPACE: Private spacious 3 bedroom lower level. Near MacDuffie Prep School & 5 prestigious colleges. Couples, solo adventurers, business travelers, families (with kids), and big groups. 14 acre. Private-golf course, pickleball, polypropylene basketball court, badminton, fishing, frisbee golf and tennis courts close by. Nature surrounds you with quiet locations to relax. 1 acre beach pond to cool off. If you are the person who likes to stay busy or relax, this is the place for you.

Guest favourite

Villa in Norwich

4.89 out of 5 average rating, 393 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

CLEAN-COZY-SAFE-PRIVATE-SPA-WOOD BURNING FIREPLACE Just 3 minutes from Mohegan Sun Casino! This 1 bedroom unit is perfect for solo explorers, couples, girls getaways, or small families looking to experience the excitement of the Casino, while also getting away from it all. Amenities include; 2 seasonal outdoor saltwater pools, jacuzzi, cardio room, and sauna! Beautiful shared grounds w/ The Spa at Norwich Inn and The Norwich Golf Course. Laundry facility onsite. Plenty of free parking!

Superhost

Home in Otis

4.94 out of 5 average rating, 143 reviews

Berkshires hideaway! Hikes & serenity near lake

Welcome to your light-filled home in the Berkshires. With a two-level wraparound deck & open floorplan, you can enjoy your time together, away from the world. Big spaces and cozy spots throughout. Perfect for families (with a swingset!) or getaways with friends. Otis Reservoir, MA's biggest lake, is nearby. Audubon preserve behind the house. Great, private home base for hiking, summer music/dance/theatre, trips to Kripalu or MassMOCA, skiing... or for going nowhere at all. Dogs OK! (note: fee)

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. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. 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 Holyoke

4.97 out of 5 average rating, 324 reviews

Explore Holyoke from this charming 3 Bedroom house

This house is settled in a quiet residential neighborhood.Guests have access to the entire second floor,one flight of stairs and you're in.There are lots of windows that brighten the space,with a large dining room,office desk, and a newly renovated bathroom.The living room leads to a beautiful spacious porch over looking the park/playground.All bedrooms have comfortable matresses,lots of pillows, soft sheets,thick super soft towels. Smart TV (Netflix/hulu/sling/roku)

Guest favourite

Cottage in Middlefield

4.92 out of 5 average rating, 245 reviews

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

Guest favourite

Home in Litchfield

4.98 out of 5 average rating, 230 reviews

Storybook Cape...HOST & Co.

A classic 1930’s Cape Cod home located in the beautiful Litchfield Hills. Litchfield Green is a five minute drive where you can enjoy antiquing, dining, shopping, and relaxing in the picturesque town center. If hiking and outdoor activities are more your thing we are also minutes from White Memorial Foundation and Topsmead National Forest is right around the corner. Mohawk Mountain Ski Area is 12 miles away.

Guest favourite

Home in Warren

4.94 out of 5 average rating, 108 reviews

Litchfield County Getaway

Welcome to Litchfield County! With only a 10 minute drive to Kent, and 20 to 25 minutes to the beautiful towns of Washington, Litchfield, Sharon, Roxbury, Cornwall, and Goshen, you will quickly realize the breathtaking beauty of Northwest CT. Surrounded by beautiful hikes, lakes, wineries, shops, galleries, and eateries, you wouldn't want to miss either spring or summer in this stunning corner of Connecticut.

Guest favourite

Home in Brimfield

4.94 out of 5 average rating, 161 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.

Guest favourite

Home in Great Barrington

4.91 out of 5 average rating, 122 reviews

Your own private Berkshires retreat

My place is close to restaurants and dining, family-friendly activities, nightlife Tangelwood, Jacobs Pillow, Mahaiwe Arts Center, Arlo Guthrie Center. You’ll love my place because of the privacy, the views, the location, the ambiance, the outdoors space. My place is good for couples and families (with kids). It has new geo-thermal central heat and AC.

Guest favourite

Home in Stockbridge

4.97 out of 5 average rating, 109 reviews

Greek Revival Farmhouse

Set on 2 acres, our home is a short walk to Norman Rockwell Museum and Chesterwood. All rooms have hardwood floors except the tiled bathrooms. We recently updated the kitchen, and previously remodeled both bathrooms with a 'vintage modern' aesthetic. Our home is furnished with a mix of antiques, vintage items and contemporary pieces.

Superhost

Cabin in Otis

4.86 out of 5 average rating, 415 reviews

Cozy cabin in the Berkshires

UPDATE: We have broadband!! Cozy and peaceful Scandinavian inspired post and beam cabin. simple, unfussy. Near many wonderful Berkshires activities. Minutes from Jacobs Pillow, lakes, ponds, hiking, biking, skiing. amazing local food and farms. Perfect country retreat for a weekend, a week or the whole month. sleeps up to 4.