Hot Ashland Cottage Rates

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Featured Cottages in Ashland

Charming single family Cottage, pet friendly w fenced in yard,

Charming single family Cottage, pet friendly w fenced in yard,

2 out of 5
Lincoln RI
The price is AU$293 per night from 30 Dec to 31 Dec
AU$293
30 Dec - 31 Dec
includes taxes & fees
With a stay at this cottage in Manville, you'll be within a 15-minute drive of Twin River Casino and Rhode Island Convention Center.
Opens in a new windowCharming single family Cottage, pet friendly w fenced in yard,
Worcester Home on Indian Lake w/ Shared Boat Dock!

Worcester Home on Indian Lake w/ Shared Boat Dock!

3 out of 5
Worcester MA
Located in Worcester, this cottage is within a 5-minute drive of Worcester Polytechnic Institute and American Antiquarian Society.
Opens in a new windowWorcester Home on Indian Lake w/ Shared Boat Dock!
Beautiful & Historic Cottage, Steps to Elm Park

Beautiful & Historic Cottage, Steps to Elm Park

3 out of 5
Worcester MA
With a stay at this cottage in Worcester (Elm Park), you'll be within a 10-minute walk of Institute Park and Newton Hill Disc Golf.
Opens in a new windowBeautiful & Historic Cottage, Steps to Elm Park
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Trail Access On-site: Gorgeous MCM Deck House!

Trail Access On-site: Gorgeous MCM Deck House!

3 out of 5
Dover MA
With a stay at this cottage in Dover, you'll be within a 10-minute drive of Charles River and Charles River Peninsula.
Opens in a new windowTrail Access On-site: Gorgeous MCM Deck House!
Cozy Pet Friendly House Next To Train

Cozy Pet Friendly House Next To Train

2 out of 5
Canton MA
With a stay at this cottage in Canton, you'll be within a 15-minute drive of Gillette Stadium and Museum of American Bird Art at Mass Audubon.
Opens in a new windowCozy Pet Friendly House Next To Train
Bright & Pet-friendly Home: 2 Mi to Harvard Square

Bright & Pet-friendly Home: 2 Mi to Harvard Square

3 out of 5
Watertown MA
With a stay at this cottage in Watertown, you'll be within a 5-minute drive of Harvard University and Harvard Square.
Opens in a new windowBright & Pet-friendly Home: 2 Mi to Harvard Square
Home Near Skiing & Downtown Worcester

Home Near Skiing & Downtown Worcester

3 out of 5
Worcester MA
With a stay at this cottage in Worcester, you'll be within a 5-minute drive of Worcester Art Museum and American Antiquarian Society.
Opens in a new windowHome Near Skiing & Downtown Worcester
Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!

3 out of 5
Worcester MA
Located in Worcester, this cottage is within a 5-minute drive of Worcester Polytechnic Institute and American Antiquarian Society.
Opens in a new windowLakefront Cottage 2 Mi to Palladium in Worcester!
Vibrant Sterling Lakefront Lodge w/ Kayaks

Vibrant Sterling Lakefront Lodge w/ Kayaks

3 out of 5
Sterling MA
Located in Sterling, this cottage is a 4-minute drive from Mary Had a Little Lamb Statue and 8 minutes from Davis' Farmland & Mega Maze.
Opens in a new windowVibrant Sterling Lakefront Lodge w/ Kayaks
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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.

Ashland Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Ashland will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Ashland definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Ashland, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Ashland Cottages essential information

Accommodation
16 Cottages
Lowest Price
AU$146
Highest Price
AU$327
Popular accommodation
Charming single family Cottage, pet friendly w fenced in yard,, Worcester Home on Indian Lake w/ Shared Boat Dock!, Beautiful & Historic Cottage, Steps to Elm Park, Trail Access On-site: Gorgeous MCM Deck House!, Cozy Pet Friendly House Next To Train, Bright & Pet-friendly Home: 2 Mi to Harvard Square, Home Near Skiing & Downtown Worcester, Lakefront Cottage 2 Mi to Palladium in Worcester!, Vibrant Sterling Lakefront Lodge w/ Kayaks

Top trending hotels in Ashland

Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$290 per night from 28 Dec to 29 Dec
AU$290
28 Dec - 29 Dec
includes taxes & fees
With a stay at Hilton Boston Back Bay, you'll be centrally located in Boston, steps from The Shops at Prudential Center and within a 5-minute walk of Berklee ...
Opens in a new windowHilton Boston Back Bay
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
10 Huntington Ave Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$327 per night from 28 Dec to 29 Dec
AU$327
28 Dec - 29 Dec
includes taxes & fees
With a stay at The Westin Copley Place, Boston, a Marriott Hotel, you'll be centrally located in Boston, steps from Copley Square and 15 minutes by foot from ...
Opens in a new windowThe Westin Copley Place, Boston, a Marriott Hotel
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 23 Jan to 24 Jan
AU$186
23 Jan - 24 Jan 2026
includes taxes & fees
With a stay at citizenM Boston Back Bay in Boston (Fenway–Kenmore), you'll be steps from Newbury Street and 11 minutes by foot from Fenway Park.
Opens in a new windowcitizenM Boston Back Bay
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Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

4 out of 5
47 Huntington Ave Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$146 per night from 30 Dec to 31 Dec
AU$146
30 Dec - 31 Dec
includes taxes & fees
Copley Square Hotel, a FOUND Hotel is centrally located in Boston, a 2-minute walk from Copley Square and 13 minutes by foot from Northeastern University.
Opens in a new windowCopley Square Hotel, a FOUND Hotel
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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.

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^Subject to availability and chosen travel dates.