Vacation rentals in Berlin

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Top-rated vacation rentals in Berlin

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Guest favorite

Cottage in Williamstown

4.9 out of 5 average rating, 165 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 full futon. Dog friendly for up to 2 dogs .More than two dogs will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Feb 7 – 14

G$32,491 GYD per night

Guest favorite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Nov 30 – Dec 7

G$20,284 GYD per night

Guest favorite

Guest suite in Hancock

4.83 out of 5 average rating, 154 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Oct 5 – 12

G$20,123 GYD per night

Guest favorite

Guesthouse in North Bennington

4.98 out of 5 average rating, 150 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned light space with cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. Please note that due to a severe allergy, we cannot accommodate animals.

Oct 23 – 30

G$32,669 GYD per night

Guest favorite

Apartment in Bennington

4.96 out of 5 average rating, 139 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Jul 24 – 31

G$26,109 GYD per night

Guest favorite

Apartment in North Adams

4.97 out of 5 average rating, 409 reviews

See MoCA from your mansion+Sauna! Ski nearby!

20-30 mins to Jiminy Peak, East Mountain, Prospect Ski, 50 mins to Mount Snow. Situated on a hilltop oasis right above Mass MoCA, this apt is part of a private historic estate. 3 mins walk to MoCA. Steps to downtown’s restaurants. 5-10 mins drive to Williams, MCLA, Clark. Whimsically restored (yes, fast Wi-Fi & great water pressure). Home to the Floating Tower Artist Retreat. YOUR STAY ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

Dec 10 – 17

G$31,912 GYD per night

Guest favorite

Apartment in Bennington

4.91 out of 5 average rating, 163 reviews

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

Aug 23 – 30

G$21,014 GYD per night

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 527 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Sep 26 – Oct 3

G$20,315 GYD per night

Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 153 reviews

Dog Friendly Farm Spring bird watching

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Aug 29 – Sep 5

G$33,352 GYD per night

Guest favorite

Apartment in Pownal

4.94 out of 5 average rating, 180 reviews

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

May 3 – 10

G$22,684 GYD per night

Guest favorite

Apartment in Petersburg

4.85 out of 5 average rating, 147 reviews

The Beer Diviner Brewery Apartment

Whole upstairs space 14 x 28 feet, small bathroom with claw foot tub and shower, twin and a full size bed, High def TV, private deck, small fridge and microwave, toaster oven, complimentary tea and coffee (no breakfast). Complimentary pint downstairs at the brewery and taproom. Located in a private setting in a hollow in the Taconic Mountains

Jan 10 – 17

G$14,223 GYD per night

Guest favorite

Apartment in Williamstown

4.93 out of 5 average rating, 236 reviews

COLD SPRING

This cozy, quaint and quiet apartment offers the perfect Berkshire county getaway. Just a drive away from Mount Greylock National Park, Jiminy Peak Mountain Resort, and the Tony-Awarded Williamstown Theatre Festival. Enjoy the mountain views, in this two bedrooms 1 bath rental with fully equipped kitchen and skylight vaulted ceiling.

Oct 7 – 14

G$34,640 GYD per night