Photo by Charlie Rhodes

Search Guest Houses in Spencertown

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Guest Houses in Spencertown

The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (320)
"excellent stay!! The Dewey is a cozy getaway location!"
$174 nightly
The price is $194
Sep 3 - Sep 4
Total includes taxes and fees
The Dewey
The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (300)
"Friendly staff, clean and perfect for a trip with the pups! "
$115 nightly
The price is $128
Sep 1 - Sep 2
Total includes taxes and fees
The Central Downtown Inn & Suites
Hudson valley and The Berkshires Cottage
Situated in a snowy forest, this cabin features two windows and a door with a small window above.

Hudson valley and The Berkshires Cottage

10.0 out of 10, Exceptional, (13)
"A great stay in this well situated getaway. The owners were helpful and communicative, and the house was easy driving distance to Great Barrington, Hillsdale and Lenox. The unit is open and airy and decorated in a very pet friendly way. Would stay again without hesitation."
$299 nightly
The price is $302
Aug 13 - Aug 14
Total includes taxes and fees
Hudson valley and The Berkshires Cottage
Renovated Private Guest House by Evergreen Home
Enjoy outdoor dining or relaxation on the deck with table and chairs.

Renovated Private Guest House by Evergreen Home

10.0 out of 10, Exceptional, (9)
"Great stay. Cute spot!"
Renovated Private Guest House by Evergreen Home
1805 House Bed and Breakfast
Situated by a serene body of water, this charming house features a spacious balcony and a covered entryway.

1805 House Bed and Breakfast

3.0 star property
9.8 out of 10, Exceptional, (38)
"Very nice stay. Perhaps a little over priced considering lack of amenities and an average breakfast."
1805 House Bed and Breakfast
Jacob's Tanglewood Ranch
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and red stove.

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Cliffwood Cottage by Evergreen Home
Enjoy cooking in this well-equipped kitchen with a central island, sink, and modern appliances.

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
Vanderbilt Lakeside
Standard Room, 1 Queen Bed, Partial Lake View | Egyptian cotton sheets, premium bedding, individually decorated

Vanderbilt Lakeside

3.5 star property
9.4 out of 10, Exceptional, (26)
"PERFECT getaway! Gracious, classy Hosts...the Inn is decorated amazingly...all of it is simply breathtaking. A lovely experience. A MUST stay!"
Vanderbilt Lakeside
Chestnut Lodge
Escape to a secluded cabin nestled among the trees, offering a peaceful retreat in the heart of nature.

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Spencertown Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Reallt liked the property. Great location. Would suggest more comfortable chairs outside."
Susan 6-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Frequently asked questions

What is the nightly rate for a guest house in Spencertown?
Rates for Spencertown guest houses vary, but travelers can find great-value prices from $128 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Spencertown guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Spencertown guest house and a B&B?
A guest house in Spencertown is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.