A river with a large bridge and a small boat on the shore.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
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Jan 15 - Jan 17

Our top choices for Portland vacation homes

A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

1. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is CA $217
CA $481 total
includes taxes & fees
Sep 30 - Oct 1
#24 Serenity A Lakefront Cottage Retreat

2. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (30 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is CA $196
CA $372 total
includes taxes & fees
Sep 29 - Sep 30
Family Stays: Middletown, CT
A modern living room with a sofa, a dining table, and a massage chair.

3. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
The price is CA $309
CA $719 total
includes taxes & fees
Oct 7 - Oct 8
#29 - Modern 5 Bedroom/2 Bath
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

4. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is CA $166
CA $392 total
includes taxes & fees
Oct 11 - Oct 12
Newly Remodeled 1-BR Close to Everything yet Very Private
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

5. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
The price is CA $166
CA $413 total
includes taxes & fees
Sep 27 - Sep 28
Once the old Schools house now a newly furnished Apartment
A two-story house with a front porch, a garage, and a well-maintained lawn.

6. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
The price is CA $667
CA $1,181 total
includes taxes & fees
Sep 28 - Sep 29
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A bedroom with a bed, a painting of birds, a window with shutters, and a patterned rug.

7. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is CA $380
CA $896 total
includes taxes & fees
Sep 26 - Sep 27
The Cottage by the Woods -private getaway to relax
A modern kitchen with white cabinets, stainless steel appliances, and a herringbone-patterned backsplash.

8. #26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (5 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is CA $202
CA $413 total
includes taxes & fees
Sep 30 - Oct 1
#26 Beautifully Renovated 2 BR Home
A modern kitchen with a central island, bar stools, and pendant lighting.

9. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (32 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is CA $914
CA $1,454 total
includes taxes & fees
Sep 25 - Sep 26
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A living room with a dark blue sofa, a round ottoman, a coffee table, and a TV on a stand. There is a large abstract painting on the wall and a window with curtains.

10. Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is CA $234
CA $700 total
includes taxes & fees
Sep 30 - Oct 1
Cozy basement apartment with private bathroom, kitchen and entrance.
A modern living room with a sofa, a coffee table, and a rug.

11. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
9.8 out of 10, Exceptional, (10 reviews)
"Good location"
United States
Arthur
The price is CA $100
CA $143 total
includes taxes & fees
Sep 26 - Sep 27
Entire guest suite in South Windsor, Connecticut
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

12. Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is CA $196
CA $430 total
includes taxes & fees
Sep 28 - Sep 29
Modern & Cozy Cape | 4 Bedroom House | Central Location
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

13. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (30 reviews)
"Was a great stay"
United States
John S.
The price is CA $197
CA $434 total
includes taxes & fees
Oct 20 - Oct 21
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

14. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is CA $134
CA $415 total
includes taxes & fees
Oct 5 - Oct 6
Sun Filled Lake House Living
A living room with a TV, sofas, armchairs, and a fireplace.

15. Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (2 reviews)
"Very friendly and easy to work with host. Communication was excellent. Home was very comfortable and convenient. Would have loved more towels, blankets and pillows. Adding towel hooks in bathroom and second sink area would be excellent. It was a great location."
United States
alissa
The price is CA $131
CA $625 total
includes taxes & fees
Sep 28 - Sep 29
Willow Haven 2BR Cozy Retreat, Close to Hartford
A modern dining area with a marble table, white chairs, and a chandelier.

16. Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
Manchester
10.0 out of 10, Exceptional, (4 reviews)
"House was great for our family stay!"
United States
Kim A.
The price is CA $204
CA $423 total
includes taxes & fees
Sep 27 - Sep 28
Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford
An outdoor seating area with a wood-burning stove, a chair, and a view of a lake.

17. Spacious modern home on private lake

Spacious modern home on private lake
Andover
10.0 out of 10, Exceptional, (29 reviews)
"The lake house was charming, comfortable and well stocked with necessities like towels, blankets, dishes, etc"
United States
Martin G.
The price is CA $246
CA $550 total
includes taxes & fees
Oct 13 - Oct 14
Spacious modern home on private lake
A living room with a blue sofa, a round coffee table, and a staircase.

18. The Game House Arcade – West Hartford

The Game House Arcade – West Hartford
West Hartford
10.0 out of 10, Exceptional, (1 review)
"Great location and well equipped. We will be back"
United States
Mike W.
The price is CA $394
CA $753 total
includes taxes & fees
Sep 27 - Sep 28
The Game House Arcade – West Hartford

19. Prime West Hartford Center: Timeless Charm

Prime West Hartford Center: Timeless Charm
West Hartford
10.0 out of 10, Exceptional, (25 reviews)
"Great location and lots of room for grandkids to spread out and fun games for them to play with"
United States
Michael W.
The price is CA $411
CA $742 total
includes taxes & fees
Oct 13 - Oct 14
Prime West Hartford Center: Timeless Charm
A modern living room with a fireplace, leather sofas, a blue armchair, and large windows.

20. #30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"the house was great for our needs - it was nicely furnished fully stocked with the essentials in the kitchen. the host checked in when it was especially cold to ensure the heat and water were working correctly. the living room was very comfortable with leather reclining chairs and a gas fireplace that heated the room very well. We enjoyed how easy our stay was and recommend this location "
United States
Kaity B.
The price is CA $309
CA $719 total
includes taxes & fees
Oct 7 - Oct 8
#30 - Spacious & Cozy!
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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Top Portland Hotel Reviews

Best Western Manchester

Best Western Manchester

8/10 Good
"The"
Leonard 1-night trip
Posted less than an hour ago
Best Western Manchester

Find out more about Portland

Portland Vacation Homes information

Number of reviews
211
Accommodation
195 Vacation Homes
Lowest Price
CA $143
Highest Price
CA $1,454

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