Bed and breakfast holiday rentals in Bennington County

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Top-rated bed and breakfasts in Bennington County

Guests agree: These bed and breakfast rentals are highly rated for location, cleanliness and more.

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Top Guest favourite

Private room in Bennington

4.94 out of 5 average rating, 89 reviews

E & E’s B & B King Bed Rm + Pool and Hot Tub

Large Private Room with King Size bed also capable of adding an extra single bed to room for extra fee 2 yrs,& older.Room sits behind a large lounge area that leads outside to the hot tub (open year round) and outdoor in-ground pool (seasonal). You have a vanity/Laptop/ phone plug in workspace in room and in lounge. Dorm Refrigerator in room Partial closet use Large dresser Extra storage for personal products and items. Free Laundry Room Use (limited loads.) Free Breakfast (Seas) patio Dining

Top Guest favourite

Private room in Bennington

5 out of 5 average rating, 121 reviews

E and E’s B and B Queen Bed Rm+ Pool & Hot Tub

We are located on 16 East Street in Bennington VT minutes from rt 7 and route 9 Main Street. Summer is more like a mini resort with a beautiful in-ground pool and Hot Tub. We also feature plenty of in-room USB phone plug-ins and extensions, in room TVs.. Perfect for couples or bring a child. (Extra Fees for children over 2 years. Sunning Deck or shaded patio dining or just relaxing with a good book poolside or the indoor lounge with a drink. We’ve got you covered. Many unexpected amenities.

Cabin in Peru

5 out of 5 average rating, 8 reviews

Renovated new rental. Clean & comfy family home.

Our family friendly home is located in a desirable location, situated on a private road and beautiful setting. Peru, VT is minutes to Manchester, Bromley, Stratton, Okemo, and Magic Mnts. Renovated in 2016, our home has a gourmet kitchen, new bathrooms, washer/dryer, double sided fireplace, woodburning stove, wireless, and great room with HDTV dish network. All beds are new, and/or protected with "sleep tite" pillow & mattress protectors. Pillows are comfortable, blankets are soft and new.

Private room in Winhall

4.86 out of 5 average rating, 7 reviews

Bromley View Inn Suite #15

Welcome to the Bromley View Inn, where strangers become friends. While staying in this suite you will have access to our large lounge featuring a fireplace, tons of seating, a bar and worktable. Outdoors guests will have access to our beautiful deck with fire pits and seating looking over Bromley Mountain. Around the grounds you'll find two ponds, a scenic and walkable property with plenty of space to enjoy. We are 4 miles from Bromley Mountain and just 7 from both Manchester and Stratton.

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Private room in Dover

5 out of 5 average rating, 6 reviews

Luxury King with balcony in Historic Inn, rm 10

Our oversized Deluxe King room with balcony is located upstairs in our historic Inn. Plush king bed and full bath with double sinks, bathtub and shower. Inn Room 10 comes with towels, toilet paper, shampoo, conditioner, body lotion and other toiletries. The balcony has a bistro set for enjoying a coffee or happy hour. This unit also has a mini fridge and coffee maker. We provide Keurig K-cups, tea, sugars and complimentary snacks. This room sleeps 2. Inn room 10 is not pet friendly.

Private room in Bennington

5 out of 5 average rating, 3 reviews

1800's Victorian Estate Sleigh Suite

Located on the floor of the Carriage House this romantic room offers a queen-size Sleigh style bed, working fireplace, full private bath w/ jetted tub and separate shower, individually controlled A/c, heat and ceiling fans as well das skylight in both the bedroom and bath. The cable TV with DVD player is housed in a comfortable sitting area apart from the bedroom which is furnished with a love seat and wing chair, plus a wet bar equipped with a coffee maker and small refrigerator.

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Private room in Dover

5 out of 5 average rating, 8 reviews

Classic King with balcony in Historic Inn, rm 8

Luxury King room with balcony in renovated Historic Inn. This room is upstairs and has a King bed and full bath with bathtub and shower. Room comes with towels, toilet paper, shampoo, conditioner, body lotion and other toiletries. The balcony has a bistro set for enjoying a coffee or happy hour. This unit also has a mini fridge and coffee maker. We provide Keurig K-cups, coffee creamer, tea, sugars and various snacks. Inn room 8 is not pet friendly.

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Private room in Dover

5 out of 5 average rating, 3 reviews

Classic King in Historic Inn on 32 acres, rm 6

Inn room 6, inside our newly renovated Historic Inn, features a King bed with a full bath including a bathtub and shower.This room sleeps 2 and is upstairs on the third floor. Room comes with towels, toilet paper, shampoo, conditioner, body lotion and other toiletries. Includes a mini-fridge and Keurig coffee maker. We provide Keurig K-cups, coffee creamer, tea, sugars and various snacks, all complimentary. Inn room 6 is not pet friendly.

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Private room in Dover

4.97 out of 5 average rating, 38 reviews

Deluxe King, kitchenette,fireplace- Cider House 1

This high-end studio at Farm Road Estate has a luxury king bed and sitting area, a kitchenette with cooktop, refrigerator, Keurig coffee maker (we provide k-cups, sugars, and creamers), microwave, and toaster. The living room has a 65 inch 4K Roku TV. This unit has 2 sinks in the bathroom, a full tub and separate shower. Toilet is in a private room. Cider House 1 has a private patio and parking area. Cider House 1 not pet friendly.

Private room in Wilmington

5 out of 5 average rating, 3 reviews

Wilmington Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

Our "round room" is particularly spacious and enjoys great privacy as well as morning sun through the bay windows. The room also has a huge Sleep 2 Live (Kingsdown) King-sized sleigh bed and an overly wide whirlpool bath. It is located in the Main House on the second floor and includes a leather reclining reading chair. All rooms include breakfast & all guests have access to our common areas loaded with games & our on-site bar.

Private room in Whitingham

5 out of 5 average rating, 3 reviews

The Engel House Room 5: Mt Snow/Wilmington VT Area

Room 5 is one of the original bedrooms of the house and is a comfy place to relax. This large room boasts many windows to get lots of natural light and second floor views of our quaint little village. The attached private bath offers a spa-like experience with a full tub/shower and a light that can give you mood lighting as well as a Bluetooth speaker that can play your own music through your cell phone or wireless device.

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Private room in Dover

5 out of 5 average rating, 11 reviews

Classic Queen – 2 Queen beds in Historic Inn, rm 5

Inn room 5 inside of our newly renovated Historic Inn has two Queen beds and 1 full bath with bathtub and shower. Room comes with towels, toilet paper, shampoo, conditioner, body lotion and other toiletries. This room is upstairs and sleeps up to 4 guests. Includes a mini fridge and Keurig coffee maker. We provide Keurig K-cups, coffee creamer, tea, sugars and various snacks. Inn room 5 is not pet friendly.

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Popular amenities for Bennington County bed and breakfasts

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly Bed and Breakfasts

Private room in Sunderland

5 out of 5 average rating, 9 reviews

The Ira Allen House B&B - Ira Allen Suite

MichelleRating, 5 stars20 months ago

Michael was a wonderful host. Was right there when we checked in even though it was late. He was helpful and kind and we felt right at home from the moment we walked in the door. Michael is a fabulous cook and breakfast each day was amazing. He remembered what you liked or your dietary restrictions. I can't say enough good about the place. From the basket of knitting, to the puzzles, reading materials, and games, you felt like you were one of the family just hanging out. Many thanks Michael and Kevin for an awesome stay!! I know we will be back!!

Private room in Sunderland

4.95 out of 5 average rating, 43 reviews

The Ira Allen House - The Ethan Allen Suite

VicRating, 5 stars20 months ago

Kevin went out of his way to cook us a vegan breakfast, the best we've ever had. Kevin is fun to be around, the common room was cozy and soothing, small B&B so met and chatted with people.

Private room in Sunderland

4.94 out of 5 average rating, 17 reviews

The Ira Allen House - Remember Baker Suite

MaraRating, 5 stars18 months ago

Kevin and Michael are the perfect hosts. We felt right at home and were well fed on delicious breakfast with local ingredients. Close to the museums we wanted to see and near excellent restaurants in Manchester. As a bonus we got the room with the fireplace and plenty of starter logs.

Private room in Wilmington

Joseph Courtemanche Suite @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

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Bed and breakfast rentals with breakfast

Private room in Wilmington

Molly Stark Suite @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

TaraRating, 5 stars52 months ago

Excellent stay! Breakfast every morning was delicious. Walking distance to several restaurants and only a 15 minute drive to Mt Snow. Charlie and Megan were great and always available.

Private room in Wilmington

5 out of 5 average rating, 5 reviews

Betty's Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

CherylRating, 5 stars54 months ago

This is a lovely place and space! Cozy, comfortable, clean and simple style, Charlie & Megan go the extra mile to make sure your stay is comfortable and you have everything you need. They communicate before and during your trip and help with anything you need. They are COVID conscious and we felt very comfortable and safe with the measures they put in place. Oh, and the breakfast menu is delicious and they have an amazing cocktail list perfect for winding down at the end of the day.

Private room in Winhall

5 out of 5 average rating, 3 reviews

Bromley View Inn Suite #12

DanielRating, 5 stars40 months ago

The inn is in a great location, close to both Stratton and Bromley. Austin was quick to communicate with, check-in was easy, room was clean and comfortable, and breakfast in the morning was great - eggs and bacon, muffins, waffles, etc.

Private room in Wilmington

5 out of 5 average rating, 10 reviews

Chimney Hill Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

LianaRating, 5 stars40 months ago

what a lovely stay! rustic inn, super friendly and helpful hosts! we wil be back 💞 thank you!

Private room in Wilmington

Windham Room @ The Wilmington Inn- Breakfast Included & downtown Wilmington location!

KateRating, 5 stars54 months ago

Cute mountain farmhouse theme Bed, and Breakfast. If you are looking to fully emerge in the Vermont experience-this is it. We enjoyed cozying up next to the woodstove in the living room/dining room while the host served us some drinks (all while feeling safe with everyone respecting COVID guidelines). Great trip!