Explore top 2025 4 Star Hotels in Highland

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Top Highland 4 Star hotels

DoubleTree by Hilton Poughkeepsie Convention Center

40 Civic Center Plz, Poughkeepsie, NY

Fully refundableReserve now, pay when you stay

$114 nightly

$133 total

Oct 5 - Oct 6

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 8 conference rooms, free WiFi in public areas, and express ...

8.4/10 Very Good! (1,006 reviews)

"Walking distance to the train station. Staff was friendly. Room was clean."

Reviewed on Sep 19, 2025

Woodstock Way Hotel

10 Waterfall Way, Woodstock, NY

$424 nightly

$470 total

Sep 30 - Oct 1

Total with taxes and fees

A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli ...

9.4/10 Exceptional! (185 reviews)

"Didn't like that there was no daily housekeeping considering the price of the room. A/C didn't work and wasn't fixed during our stay. However, the staff was very accommodating and the location is outstanding."

Reviewed on Sep 24, 2025

Mirbeau Inn & Spa

46 West Market St, Rhinebeck, NY

A full-service spa, 2 restaurants, and a hot tub are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 2 conference rooms, ...

9.4/10 Exceptional! (300 reviews)

"Spa was top notch. Rooms were very elegant and bed was super comfortable. Atmosphere was very calm and relaxing. Will definately return."

Reviewed on Sep 12, 2025

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Kingston Carriage House

85 Abeel St, Kingston, NY

Fully refundableReserve now, pay when you stay

$311 nightly

$351 total

Sep 30 - Oct 1

Total with taxes and fees

This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. Enjoy the free continental breakfast each morning. A ...

9/10 Wonderful! (24 reviews)

Comfortable Local Stay

"Riverfront Kingston area close to main street. Easy self check-in and check-out. On a main road with less traffic noise after 9-10pm. Rustic charming room. Temperature control with AC in main room and heating fan in bathroom. Ample sized bathroom and main room with king sized bed and loveseat. Record ..."

Reviewed on Sep 13, 2025

Hasbrouck House

3805 Main St, Stone Ridge, NY

$555 nightly

$622 total

Oct 26 - Oct 27

Total with taxes and fees

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free ...

8.8/10 Excellent! (49 reviews)

"Great getaway property. We checked in for two nights, and stayed in a building with kitchen/2 bedrooms, which was great for our needs. We spent time in the property relaxing at the beautiful pool, sauna, and had a fabulous dinner at Butterfield. Played some shuffleboard, pool and video games in their ..."

Reviewed on Aug 6, 2025

it's a good thing

233 9 Partners Rd, Clinton Corners, NY

$146 nightly

$166 total

Oct 1 - Oct 2

Total with taxes and fees

This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A terrace, ...

8.6/10 Excellent! (21 reviews)

"Really sweet woman who owns the house. Gave us good recommendations for dinner and things to do. The room was really cozy and fall!"

Reviewed on Sep 21, 2025

The Herwood Inn

148 Tinker St, Woodstock, NY

$220 nightly

$246 total

Oct 27 - Oct 28

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers ...

9.6/10 Exceptional! (84 reviews)

"Dust on basically every surface, and the fridge makes a loud buzzing noise. Road noise is really loud and kept us up all night. Otherwise the vibe was great, location perfect, decor was nice, great amenities in the kitchenette. Would not return on account of the cleanliness and loud road noise ..."

Reviewed on Sep 25, 2025

Journey Inn Bed & Breakfast

1 Sherwood Place, Hyde Park, NY

$224 nightly

$253 total

Sep 30 - Oct 1

Total with taxes and fees

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A garden, a library, ...

9.6/10 Exceptional! (277 reviews)

"The owners are lovely and breakfast was wonderful. It's 10 mins from Rhinebeck with lots of good restaurants which they recommended. Lovely stay."

Reviewed on Sep 4, 2025

Millbrook Country House Bed & Breakfast

3244 Sharon Turnpike, Millbrook, NY

$198 nightly

$224 total

Oct 1 - Oct 2

Total with taxes and fees

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A terrace, a garden, and luggage storage ...

8.8/10 Excellent! (78 reviews)

"Lovely customer service!"

Reviewed on Aug 19, 2025

The Millbrook Inn

3 Gifford Rd, Millbrook, NY

A restaurant and a bar/lounge are featured at this inn. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies ...

"Love it! beautiful inn and amazing food!"

Reviewed on Feb 27, 2023

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4 Star Hotels Highland

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Highland 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Highland will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Highland, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.