Holiday houses in Bloomfield
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Top-rated holiday rentals in Bloomfield
Guests agree: these stays are highly rated for location, cleanliness and more.
Home in Great Barrington
4.88 out of 5 average rating, 101 reviewsGreat Barrington, Cabin Sleeps 14, Walk To Town
Our family had a great stay at Lucas’s house in Great Barrington. We were close enough to town to enjoy the amenities and also a short trip to butternut, where we had a great day of skiing with a group of mixed skiing experience. The house was comfortable and clean and we enjoyed the views from the big front windows.
Holiday home in Warren
4.98 out of 5 average rating, 154 reviewsPrivate new house on 10 acres of pristine nature
For the area, definitely a great place to stay! Unfortunately because of the snow we couldn’t do some things outside but 100% recommend this to anyone going to the area. You will not be disappointed!
Chalet in Goshen
4.89 out of 5 average rating, 134 reviewsThe Goshen Glass Chalet
a beautiful stay for sure, very peaceful and removed from the city. My girlfriend and I will be staying there again for sure
Cottage in Great Barrington
4.83 out of 5 average rating, 35 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
Plenty of space for two families to share and wonderful for kids. Location is ideal for skiing and tubing plus town has good food and shops.
Home in Farmington
5 out of 5 average rating, 60 reviewsLake Escape: Lake Cottage Charm, Lake Front, AC
Tracie and Sean were very friendly. The house was very clean and well organized. Loved it!
Apartment in East Lyme
4.97 out of 5 average rating, 219 reviewsBrand New Direct Lakefront - Panoramic Sunsets
We had an incredible experience at this wonderful location. The breathtaking views left us in awe, with panoramic sights that seemed to stretch on forever. Every moment spent there was truly enjoyable, and we found ourselves fully immersed in the beauty surrounding us. We wholeheartedly recommend this place to anyone looking for a memorable escape!
Home in Oxford
4.97 out of 5 average rating, 37 reviewsLakefront Oasis - Getaway to this Oxford Treasure!
From the booking to arrival it was seamless. Our host Alicia was fantastic along with Michael addressing a minor issues we had. Now for the details… the house is set on a picturesque lake which is quiet and tranquil. The house was immaculate. We couldn’t ask for more. The house is fully stocked with necessary things and beyond. Our Hosts were very attentive and receptive and addressed our questions very quickly. We were absolutely astounded at the views from your home. Thank you for welcoming our family into your home. We had a wonderful experience and hope to return in the future. Jeff A.
Home in Otis
4.9 out of 5 average rating, 51 reviewsBerkshire Lakefront Lighthouse Getaway
Great place to spend a warm Fall day. Super cool place, really comfortable bed and an incredible view right on the lake.
Home in Sheffield
4.9 out of 5 average rating, 115 reviewsWow! Best BERKSHIRE SnowHome #1 Private SuperClean
We thoroughly enjoyed our stay in Sally’s cozy apartment! It is well appointed and tastefully decorated. Sally was very responsive and caring. The beautiful views out of our bedrooms onto the garden and the wide open landscape behind it were major treats, especially on the morning after a heavy snowfall. We found everything we needed and more than expected - and hope to be back one day! Thank you very much, Sally!
Home in Canton
4.99 out of 5 average rating, 101 reviewsBest River View, on Rail Trail in Collinsville!
My family had a wonderful stay at Carol‘s house! We were traveling with our two-year-old son and four-year-old daughter and this was the first time the kids saw snow! Carol was very helpful and responsive and even went out of her way to make sure the kids had some extra toys stocked at the house. The views are stunning and the house was well stocked (for the winter cold) with blankets, extra pillows, etc. We will be back to stay again!
Guesthouse in East Hampton
4.93 out of 5 average rating, 41 reviewsFamily-Friendly Lakeside Cottage
Great location and comfortable beds. We enjoyed having coffee next to the lake. Josh was very responsive when we had a question. All around great stay.
Home in Brimfield
4.94 out of 5 average rating, 160 reviewsBrimfield Lakeside Home Away from Home
We had a great stay! The beds and linens were comfortable and smelled so fresh. We look forward to coming back in the summer when we can enjoy the lake. Thanks again!
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Other great holiday rentals in Bloomfield
Guesthouse in Southbury
4.93 out of 5 average rating, 318 reviewsCharming Guest Cottage with Modern Amenities
John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!
Apartment in Great Barrington
4.78 out of 5 average rating, 18 reviewsWriter's retreat: study, books, fireplace (Ecobnb)
The location and space were great! I worked remotely during most of my stay and was very comfortable with my set up. The dining table was a perfect desk, with good lighting and wifi! Slept well due to it being so quiet at night. A positive experience overall.
Home in Granby
5 out of 5 average rating, 6 reviewsLake house retreat Granby CT
WENT FOR A FAMILY CELEBRATION FOR THANKSGIVING WEEKEND. THE HOUSE WAS INCREDIBLY STUNNING, GREAT ENTERTAINMENT AREAS, PLENTY OF SEATING, BEAUTIFUL KITCHEN. EVEN THOUGH IT WAS THE END OF NOVEMBER, WE STILL WERE ABLE TO USE ALL THE OUTSIDE AMENITIES, THE OUTDOOR BAR, SEATING AREA, FIRE PIT, THE HEAT LAMPS WERE PERFECT & UNEXPECTED. THE OUTDOOR AREA WAS AS AMAZING AS INSIDE. THE HOUSE WAS BETTER THAN WE EXPECTED, WOULD HAVE TO SAY PERFECTION! CANNOT WAIT TO GO STAY AGAIN. THANK YOU TO NATHANIA, YOU'RE COMMUNICATION WITH US WAS QUICK & GREATLY APPRECIATED! LOVED EVERY MINUTE!
Home in Andover
5 out of 5 average rating, 54 reviewsSpacious Classic Lakefront Home with jet tub
I came here in the dead of winter for a writer's retreat with a fellow writer- AND I WOULD DO IT AGAIN! It was a beautiful and inspiring place to write. Perched on Andover Lake, it was too cold to frolic outside but that was actually liberating. There was a rocking chair-ottoman combo in the master bedroom looking out on the lake and watching it freeze while I worked on some writing was so peaceful and perfect. When I needed to switch it up, there was a writer's desk with the same view and I can not overstate how nice and productive it was to work from it. I am sure in the summer it's a really fun stay (there were kayaks and a dock for swimming) but I actually loved being isolated in such an idyllic place. It's near a few other homes but the road was low traffic enough for a cold weather run around half the lake. Marcie was super helpful with suggestions for places to eat. We didn't actually use the recs - but that only speaks to how nice the house was and how hard it was to leave!
Cabin in Lebanon
4.86 out of 5 average rating, 14 reviewsCasa Lago
I didnt want to leave this little cabin in the woods. It felt rustic but had all the modern amenities you would expect in a home. From the rocking chairs on the porch to the comfy beds, there is nothing I could complain about, even if I tried. Marilyn gave excellent suggestions of places to eat and local current events. We left with fall apples, bellies full of clam chowder, and gigantic smiles!!! We have already started planning our return!
Home in Otis
4.92 out of 5 average rating, 149 reviewsThe Pinnacle House at Otis Ridge Ski Area!
We had a great stay at the Pinnacle house! We loved being in a ski-on ski-off location, and the house was so cozy and well stocked with books, toys for our kids and baby/ toddler gear (we were happy to see there was a toddler bed attachment for a bed in the twin bedrooms, too!). The place was very comfortable for our whole family. Mary Kay was really responsive and a great host! We want to come back soon. Thank you!!
Bungalow in Old Lyme
4.94 out of 5 average rating, 295 reviewsPet Friendly Bungalow!!!
Lovely little cottage, very thoughtful amenities such as bottled water and snacks, nicely laid out. June was very proactive in communicating with us and following up to make sure everything was to our satisfaction. We were there in December, but it would be a great place to stay in warmer weather when you could take advantage of being lakeside. Would definitely go back next time we are in the area.
Home in Tolland
5 out of 5 average rating, 26 reviewsLakefront Retreat at Porcupine Place
Lovely house and location. Views are great. Lots of natural light. Nice surroundings. Very clean. Away from the hustle and bustle. Exceeded our expectations. It was just my husband and I but we hope to return with the kids.
Quick stats about holiday rentals in Bloomfield
Total rentals
60 properties
Nightly prices starting at
$32 AUD 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
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