A suspension bridge over a river with autumn foliage and distant hills.

Book Highland Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Highland bed & breakfast

A house with a porch, outdoor seating, and string lights.

1. Hudson Pond · Hideaway King Suite · GF Breakfast

Hudson Pond · Hideaway King Suite · GF Breakfast
Poughkeepsie
10.0 out of 10, Exceptional, (5 reviews)
"Nicole's renovation of this charming old farmhouse, both inside and outside, is a work of art and no doubt a labor of love.Clean rooms.Modern bathrooms.Beautiful property.Great breakfast.One caution: the staircase leading to the upstairs bedroom is probably unsuitable for older people. ."
United States
David Z.
$145 nightly
The price is $164
Nov 10 - Nov 11
Total with taxes and fees
Hudson Pond · Hideaway King Suite · GF Breakfast
A stone bridge over a calm river surrounded by autumn foliage.

2. Journey Inn Bed & Breakfast

Journey Inn Bed & Breakfast
4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (363 reviews)
"The keepers were extraordinarily friendly and helpful. The breakfast was outstanding and freshly made with local ingredients."
United States
Lisa
$242 nightly
The price is $273
Nov 1 - Nov 2
Total with taxes and fees
Journey Inn Bed & Breakfast
A kitchen with wooden cabinets, a dining table with chairs, a chandelier, and a view through the window.

3. Hudson Pond · Garden Queen Suite · GF Breakfast

Hudson Pond · Garden Queen Suite · GF Breakfast
Poughkeepsie
10.0 out of 10, Exceptional, (6 reviews)
"What a hidden gem! Just minutes away from the hussel and bussle of the city! Beautiful gardens and well stocked kitchen!"
United States
Barbara
$135 nightly
The price is $153
Nov 9 - Nov 10
Total with taxes and fees
Hudson Pond · Garden Queen Suite · GF Breakfast
Exterior

4. Tin Brook Bed & Breakfast

Tin Brook Bed & Breakfast
3.0 star property
Walden
9.4 out of 10, Exceptional, (140 reviews)
"I stayed over the gift shop in the Strawberry Room and it was perfect!"
United States
Michael
$138 nightly
The price is $156
Oct 25 - Oct 26
Total with taxes and fees
Tin Brook Bed & Breakfast
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.

5. Omega Special 1860s farm house 3 miles away

Omega Special 1860s farm house 3 miles away
Clinton Corners
8.6 out of 10, Excellent, (12 reviews)
"Lynn was incredibly kind, helpful, and friendly. Our stay was very comfortable and centrally located to everywhere we wanted to be. The property was beautiful and scenic, and the home was as cozy and comfortable. She even put out breakfast and coffee for us in the morning, which was very nice! We would absolutely stay again!"
United States
Kenneth P
$170 nightly
The price is $192
Oct 25 - Oct 26
Total with taxes and fees
Omega Special 1860s farm house 3 miles away
A garden with a variety of plants and flowers, a white picket fence, and a small table with chairs.

6. Millbrook Country House Bed & Breakfast

Millbrook Country House Bed & Breakfast
4.0 star property
Millbrook
9.0 out of 10, Wonderful, (86 reviews)
"the minute we arrived the host was helpful, and very nice. He even asked if we needed dinner reservations. The room was clean and pristine. the breakfast was excellent. the host was very cordial and helpful. would definitely recommend. would definitely stay again if in that area"
United States
kenneth
$240 nightly
The price is $272
Oct 25 - Oct 26
Total with taxes and fees
Millbrook Country House Bed & Breakfast
A covered porch with rocking chairs and a red door.

7. Kingston Carriage House

Kingston Carriage House
4.0 star property
Rondout
9.2 out of 10, Wonderful, (57 reviews)
"It was a cozy place and my family loved it. The record player was a nice touch"
United States
Michelle
$280 nightly
The price is $313
Nov 2 - Nov 3
Total with taxes and fees
Kingston Carriage House
A rustic hall with wooden beams, long tables set for dining, and a high ceiling with exposed beams.

8. Stonehill's Farmhouse

Stonehill's Farmhouse
3.5 star property
Accord
9.0 out of 10, Wonderful, (62 reviews)
"Overpriced. Could be a great place"
United States
Pratima
$261 nightly
The price is $292
Nov 2 - Nov 3
Total with taxes and fees
Stonehill's Farmhouse
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.

9. Private room on secluded 7 acres , access to entire house including patio, porch

Private room on secluded 7 acres , access to entire house including patio, porch
Clinton Corners
8.6 out of 10, Excellent, (33 reviews)
"Wonderful hosts in a quaint home in a lovely spot."
United States
Sharen B.
$165 nightly
The price is $187
Oct 25 - Oct 26
Total with taxes and fees
Private room on secluded 7 acres , access to entire house including patio, porch
A two-story house with a porch, a front door, and a small garden area with potted plants.

10. Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (197 reviews)
"Great location and nice sized room. Missed the en suite bathroom but was no problem. Breakfast was nice. Lovely town."
United States
William
$148 nightly
The price is $175
Oct 26 - Oct 27
Total with taxes and fees
Borland House Inn
A brick building with a covered patio area featuring outdoor seating and string lights.

11. Cromwell Manor Inn

Cromwell Manor Inn
4.0 star property
Cornwall
9.4 out of 10, Exceptional, (110 reviews)
"The stay was wonderful. The personnel were very accommodating."
United States
Steven
$339 nightly
The price is $400
Nov 24 - Nov 25
Total with taxes and fees
Cromwell Manor Inn
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.

12. it's a good thing

it's a good thing
3.0 star property
Clinton Corners
7.8 out of 10, Good, (35 reviews)
"The warmth of the owners!"
United States
Evangelia
$199 nightly
The price is $225
Oct 25 - Oct 26
Total with taxes and fees
it's a good thing
A house with a brick pathway leading to the front door, surrounded by lush greenery and trees.

13. Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,

Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Clinton Corners
7.8 out of 10, Good, (12 reviews)
"The propert my, grounds and location is just charming. Hosts were stellar and welcoming. Accomodations warm and inviting."
United States
Dawn B.
$184 nightly
The price is $208
Oct 25 - Oct 26
Total with taxes and fees
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
A large, two-story white house with a wrap-around porch and a small front garden.

14. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (238 reviews)
"The owners were so kind and attentive, and the grounds are absolutely beautiful! Delicious food, gorgeous mountain air, and the horses were adorable. Thank you for having us!"
United States
Sinead
$108 nightly
The price is $122
Nov 9 - Nov 10
Total with taxes and fees
The Dominion House Bed & Breakfast
A bedroom with a wooden dresser, a mirror, a bed with a blue quilt, a window with blinds, and a wall-mounted light switch.

15. Twin Bedroom with Private Bathroom at Storm King Lodge

Twin Bedroom with Private Bathroom at Storm King Lodge
New Windsor
$325 nightly
The price is $369
Oct 25 - Oct 26
Total with taxes and fees
Twin Bedroom with Private Bathroom at Storm King Lodge
A sign for StormKing Lodge with a decorative flower and fox atop it, surrounded by greenery and a paved path.

16. Loft Room with Private Bathroom at Storm King Lodge

Loft Room with Private Bathroom at Storm King Lodge
New Windsor
$325 nightly
The price is $369
Oct 25 - Oct 26
Total with taxes and fees
Loft Room with Private Bathroom at Storm King Lodge
A two-story house with a front porch, a stone chimney, and a well-maintained lawn.

17. Loft Suite with Private Bathroom at Storm King Lodge

Loft Suite with Private Bathroom at Storm King Lodge
New Windsor
$389 nightly
The price is $443
Oct 25 - Oct 26
Total with taxes and fees
Loft Suite with Private Bathroom at Storm King Lodge
A wooden-paneled room with a bed, a chair, a dresser, and a window with curtains.

18. Pine Suite with Private Bathroom at Storm King Lodge

Pine Suite with Private Bathroom at Storm King Lodge
New Windsor
$381 nightly
The price is $433
Oct 25 - Oct 26
Total with taxes and fees
Pine Suite with Private Bathroom at Storm King Lodge
A vintage black car parked on a road with a white fence and trees in the background.

19. Jenny's Country Manor

Jenny's Country Manor
2.0 star property
Red Hook
7.8 out of 10, Good, (142 reviews)
"I like that it has some character and authenticity. Its everything you need in an awesome area, yet tucked away from too much craziness and traffic."
United States
amanda
$133 nightly
The price is $151
Nov 1 - Nov 2
Total with taxes and fees
Jenny's Country Manor
A serene garden with a stone pathway, a small bridge, and a bench.

20. Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY
3.0 star property
Woodstock
8.6 out of 10, Excellent, (170 reviews)
"We had a great time! The host was super sweet and helpful, and the breakfast was delicious. Would stay again!"
United States
Lucian
$219 nightly
The price is $245
Nov 2 - Nov 3
Total with taxes and fees
Morning Glory B n B Woodstock NY
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

8/10 Good
"Comfortable bed. Helpful staff. Good location."
Patrick 1-night trip
Posted less than an hour ago
Holiday Inn Express Poughkeepsie by IHG

Find out more about Highland

Highland B&B information

Number of reviews
675
Accommodation
35 B&B
Lowest Price
$122
Highest Price
$443

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Highland?
Prices for B&Bs in Highland often vary, but you can find a great deal from $122 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Highland B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Highland?
The best time to book a B&B in Highland is during the peak season from March to May, with April standing out as a particularly popular month. This vibrant period welcomes travelers eager to immerse themselves in Highland's stunning natural beauty, with blooming wildflowers and lush green landscapes that create a picturesque setting for outdoor adventures.

As the weather warms up, temperatures typically range from the mid-40s to the low 70s Fahrenheit, providing a comfortable climate for hiking, biking, and exploring the charming local attractions. The stunning views of the nearby mountains and lakes are great for photography enthusiasts and nature lovers alike, ensuring plenty of opportunities for memorable experiences.

For those seeking a more budget-friendly visit, consider planning your trip in December. While this month may be quieter, it offers a unique charm with festive decorations and a chance to experience the tranquil beauty of Highland during the winter season.
What is the difference between a Highland Bed and Breakfast and a hotel?
Every Highland B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Highland B&Bs.

Explore a world of travel with Expedia